


On the Road

by Daydreaming_Scribe



Series: And with but a Single Word AU [2]
Category: Supernatural
Genre: BAMF Jessica, Episode: s01e06 Skin, F/M, Gen, Hell, Hunter Jess, Hunter Jessica Moore, Hurt/Comfort, Jess Lives, John Winchester's A+ Parenting, M/M, Multi, Polyamory, Rape/Non-con Elements, Sam Winchester's Demonic Powers, Suicide, Torture, Trauma
Language: English
Status: In-Progress
Published: 2015-10-04
Updated: 2016-03-20
Packaged: 2018-04-24 19:00:21
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 2
Words: 24,124
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4931467
Author URL: https://archiveofourown.org/users/Daydreaming_Scribe/pseuds/Daydreaming_Scribe
Summary: <blockquote class="userstuff">
              <p>Sequel to "And with but a Single Word."</p><p>After Sam is dragged into Hell by Brady's demon, Jess becomes a Hunter to save her fiancee. Along the way, she picks up other friends from Stanford, and friends from the Hunting World. All the while, Sam is making bonds with several specific demons in hell.</p><p>When not being tortured, that is.</p>
            </blockquote>





	1. Skin

**Author's Note:**

> Okay, this specific work is the Canon Divergence of the first 2 seasons. Important or likable episodes, including Skin, Home, Hellhouse, All Hell Breaks Loose, and whatnot are going to be featured.
> 
> I know that there's a huge difference between Canon Hell and my Hell, but, like I said, this is an AU. The excuse is that while normal hell is still 120 days to every Earth one, Lucifer was so pissed about Sam not playing his part that the portion of hell he was sent to will be about a billion years to an Earth Day (Cue a lot of emotional crying when Jess and Brady find out).

**Summary for the Chapter:**

> Jess stops in St. Louis after Becky contacts her. Dean has a run-in with everyone's favorite FBI agent. And Sam-
> 
> -Well, it's better you read it than explain it.

**Notes for the Chapter:**

> This contains somewhat graphic detail of torture, and implications of molestation and abuse. Please be advised to avoid if you feel this may trigger you.

Hell, Sam decides, is Hell.

The minute he lands there, the demons are in an outrage that someone as soft and gentle as him could ever be ‘The Vessel.’ His clothes are torn from his body, and his flesh is beaten, torn, flayed, and burned in every way possible. He’s kicked into a swamp of human filth, held there until the stench fills his nostrils and his lungs.

He’s then lifted, still nude, and held against a wooden pole. The demons place his hands above his head, putting one in front of the other, and drive a spike through it. They laugh as he screams, tears rolling down his cheeks. His feet are held in place, one on top of the other, and a second spike is impaled through them.

His crying and begging is just met with jeer after jeer, demonic laughter, and comments of how cutely he begs. They fix hooks, one at a time, into the flesh in his arms, his sides, his legs. Shards of glass are shoved in roughly at certain angles of his mouth, breaking the skin and filling his lungs with blood. The two horns of an unidentifiable animal are shoved into his head, making him resemble the stereotypical demons of lore, and he wishes that it kills him. But, of course, being in Hell, he’s already dead, so he feels his brain light up in unimaginable pain, but doesn’t get the mercy of darkness closing over his eyes.

In the smallest corner of his mind, he’s aware of the parallels with another story. Tortured by ‘his people’, beaten, bloody, fixed to a piece of wood by several spikes through his hands and feet. A sign fixed above his head, which reads ‘ _Rex Daemoniorum_ ’ (King of Demons) only furthers the parallel. But there is no comparison between Sam and _Him_ , not really. He was pure, selfless. He saved everyone by doing what he did. Sam’s here because he deserves it. He was selfish and stupid enough to think that he could escape his life, and he got the two closest friends he made in his time at Stanford put in danger. The only benefit to his torture is that one person was saved. Sure, he intended for it to be two, but Azazel made it pretty clear that Brady was going to be his puppet for as long as he says.

And this torment is not going to be three hours. It’s literally going to continue on until the end of times. And the demons are angry, that the Abomination they put so much hope in is not even a proper demon, much less a proper human.

They are going to make him suffer, and he knows in his heart that he’s earned it.

* * *

 

Day 93.

Bobby point-blank _refuses_ to let her go to St. Louis alone, because she hasn’t even been on a hunt yet. After all, even with her new FBI Badge that declares her to be Special Agent Emmeline Pankhurst, the police will not leave her alone in Zach’s holding cell. And the minute Zach sees her, he’s going to say her name, and the story will come crashing through, and she’ll be in jail alongside him.

The demonologist is actually pretty tempted to tell her that she shouldn’t be going anywhere near her old Stanford friends, but when she argues that Brady was possessed, and that Zach isn’t prone to just kill people out of the blue, he relents. So, they take the long drive from Sioux Falls to St. Louis, and Bobby drops her off in front of the Warren house, while he heads downtown to introduce himself to the Saint Louis P.D as Agent Willis.

Stepping up to the door, Jess hesitates, her hand hovering over the polished wood. Her friends (and family) had been strongly against her leaving Stanford, regardless of Sam’s disappearance, and she hadn’t seen Becky nor Zach since the time Sam disappeared. She only knows about the case because Becky texted her saying that Zach had been arrested for murder.

She knocks.

The door is opened by a girl about a year her junior. She has blond hair and light eyes, just like Jess, except her hair is as straight as Jess’ is curly. At Stanford, little Becky Warren would constantly complain about how unfair it was that her curls were perfect.

“Jess!” Becky exclaims, pulling her friend into a hug. Even though she’s spent the last few months staring at the ceiling every night, thinking of Sam being tortured in Hell, she melts into the embrace, letting loose the feelings of anxiety and loss she’s had buried inside her for so long, because it’s good to see a familiar face.

One who understands why she couldn’t continue with school without her boyfriend, unlike her stuck-up rich family that she’s been dying to escape almost as much as Sam was dying to escape his asshole hunter-dad, and his asshole hunter-brother.

* * *

 

Caleb splits when they realize that the police pursuing them are after Dean. The younger hunter feels a bit betrayed (of course, with a cowardly, deserting little brother like Sammy, he should be used to it by now), but he brushes it off. After all, he’s a hunter. He’s been on the run ever since he was 4 and a half. How long’s he going to have to worry about some silly back-water police?

The answer, he finds out, is exactly three days after they separate, because that’s the time it takes for him to get cornered in a Mini-Mart outside Columbus. He gets hauled, ass-first, into an interrogation room, and waits about 3 hours before a sharp-looking bald black dude in a suit shows up. From the minute they meet, the guy has fixed Dean with the look of someone eyeing something gruesome and unattractive.

“Gotta tell ya,” He drawls, walking up to the table. “It takes a special kinda stupid to wander out in the open like you do, given everything you’ve done.” Dean frowns at this. He knows that he’d be in trouble for the usually hunter charges: grave desecration, breaking-and-entering, credit card fraud. But normal (well, relatively normal) people do that shit and don’t necessarily go into hiding. Why should he be expecting to?

“The Hell does that mean?” He demands, raising an eyebrow. The black dude gives a snort of derision, like he can’t believe Dean’s asking this.

“Well, I don’t know about you, but if I abducted my little brother after threatening to kill his fiancée, I wouldn’t be out and about, especially when the aforementioned fiancée was able to link me to a series of grisly murders across the U.S.” Dean feels his face tighten.

“I didn’t touch Sammy.” He growls. The fed huffs, giving a smirk.

“Nice try, Dean, but just saying that doesn’t eliminate the facts we have.” He informs Dean, tapping the pile of files he’s placed on the table.

“Look,” Dean sighs. “Agent…-?”

“Henriksen. Victor Henriksen.”

“Agent, Henriksen, this is all a huge misunderstanding.” He says, trying to make a pleading gesture as best he can in handcuffs. “I would never harm my little brother.”

“Records are singin’ a different tune.” Henriksen says with a scoff, flipping through the case in front of him, before pulling out a file. “Says according to this, on November 1st, 2005, one Sam Winchester was admitted at 12:13 A.M to Stanford Medical Center, with bruising on his face so bad that he could hardly see out of either eye, while maintaining some light bruising on his body, not to mention several severe blows to the face that fractured his nose, cheeks, jaw, and mouth. Neither he nor his girlfriend would talk about how the injuries had been obtained, and he was discharged the next afternoon. At 11:42 that evening, the Palo Alto Fire department had been called to the apartment complex where Sam Winchester and his girlfriend, Jessica Moore lived. Moore had been found with a cut stomach, and was taken immediately to Stanford Medical.

“In the Witness statement, Jessica Moore revealed the assailant who attacked her boyfriend two nights before was none other than his estranged older brother, Dean. She said that the perp had broken into their apartment, before Sam found him, and that they had clearly been speaking in some kind of code. Sam refused to come with Dean, legitimately fearing that he would be hauled away from his school by force, and was eventually beaten, before the perp escaped.

“She then went on to say that Dean returned on November the 2nd, with an older man identified as their father in tow, carrying a knife, several spikes, and a flamethrower. She claims that Dean stabbed her and threatened to stick her to the ceiling and burn her alive right in front of Sam for deserting them. Her boyfriend then begged them to spare her life, and said that he would go with them if they did.”

Jess. That dumb blond bitch his brother had been screwing. The one who had convinced him to abandon Dean, and who’d given Dean all that shit for “devaluing Sam” or whatever. She had tried enlisting his help in her half-assed rescue mission for Sam, and evidently didn’t like that he said no.

Oh, sure, ‘cause independence was hot in one Winchester brother, but not in the other.

“The bitch is lying.” Dean growls. “I have no reason to hurt her, neither does my Dad.” Henriksen raises an eyebrow.

“She must have been lying pretty good, because the evidence speaks for itself.” He flips a bit more threw the dossier. “Says here your father’s a veteran from Vietnam. Abandoned by his own father back in ’58, moved to Lawrence, Kansas after he got back from the War. Set his sights on a young Mary Campbell. Of course, according to anyone around, the Campbells kept to themselves. The father, Samuel, was a hard-ass.

“Campbell mother and father bite the dust on November 2nd, 1973, both stabbed to death in their own home. Mary and John get married almost instantly, and have you 6 years later. Four and a half years after that, your brother Sammy’s born, but your mom dies in the November of that year, in a nursery fire with no body. Police question, but they have no reason to believe foul play. After all, with two sons and a happy marriage, who’d question it?

“So, you three live on the road for the next eighteen years, with almost no long-term contact. There’s several other cases in the same year as your mother’s death, with an eerie similarity. Nursery fire, no body, no motive, around 6 months after the infant’s born.

“Sammy goes to Stanford, on a full-ride because of the tuition leniency, and starts making friends over the course of four years. Friends who claim that he seemed very abused. He basically tells them his family wanted no part of him, going to one of the best schools in the country for free. He’s a good kid, if not quiet. In all the service hour clubs at Stanford, tutors local youth for free, keeps his grades up, gets a girlfriend, the works. Even if no one knows a thing about Sam Winchester, they can tell you he’s an amazing young man, who’s going places, even if he doesn’t see it.”

“I don’t see what any of this has to do with me.” Dean objects, not wanting to hear any more of how _good_ Sam was at Stanford. Victor gives an ugly look.

“Your daddy’s a Ted Bundy wannabe, Dean. He killed your grandparents to get to your mother, and your mother to keep her silent. Ten years apart to the date. He went on a spree, killing all these other women with 6 month old babies, for the resentment of losing his wife, and went on the run to avoid being caught. Your brother knew it, and he tried to get out.” There’s a pause. “But Old John couldn’t have any squealers. So, he picks the day his wife dies, 22 years to the date, to come and visit his youngest son, and drag him back into this life. And big brother,” The Fed sneers. “Well, Sammy had everything. A beautiful girl, a top education, the potential to go to the best law school in the world for free. And big brother couldn’t stand that, now could he, Dean? So, you tried ‘saving’ him from this life, and when he refused, you beat the fucking shit out of him.”

This fucking cop is damn lucky that Dean’s handcuffed to the table, because he stands up so fast that the chair he was sitting on falls back.

“You shut your fucking mouth!” Dean snarls. “This is none of your business!” The agent looks unimpressed by Dean’s outburst.

“Until such time as Sam Winchester is found, dead or alive, this very much _is_ my business. He may not have a real family, but he _does_ have Stanford Law (and, actually, most other law schools in the country) willing to _hand_ him money to attend for saving a life, and a fiancée who is hoping to become Mrs. Winchester.” There’s a pause. “Or, possibly make him Mr. Moore. Given the connotations to the family name, he might want to drop it. So, you can either tell me where Sam or your father is, or go away, for a long time. You may not have been old enough when your father murdered all those other people, but we can still have you as a knowing accomplice in kidnapping.”

“Sammy’s dead.” Dean says flatly, blood boiling. “I didn’t kill him. Blondie saw something else. She tried getting me to help, and because I didn’t, she’s screwing with me by lying to the police about why Sam disappeared.” Henriksen gives another sneer.

“Good luck selling that to the jury, Winchester.”

* * *

 

“What?” Jess demands. On the other end, she hears her mentor give a sigh of irritation.

“Goddamn, you and Sam are two peas in a freakin’ pod. Smart enough to go to Stanford, but outside of that you’re the biggest pair ‘a idjits I’ve seen, apart from Dean an’ their Daddy.” He growls. Despite the mention of perhaps her two least favorite people in the world (Donald Trump, Rick Santorum, John Mayer, Stephanie Meyer, Osama Bin Laden, Kim Jong-il, and that drunk sorority slut who tried multiple times to cop a feel on Sam excluded), she smiles at the endearing comparison between her and her boyfriend. “I tried everything. Holy water in a water bottle, iron….Said ‘Christo’ so many times the poor boy thought I was havin’ a stroke. Ain’t a demon.”

“That doesn’t make any sense.” She counters. “I may not have seen Zach in over a year, but I know he isn’t a killer.” She attempts to keep her voice down, so Becky (currently waiting for Jess to return to her bed so they can resume watching ‘The Sisterhood of the Traveling Pants’, which Jess is not all excited for) doesn’t hear her.

“Well, the case was a dead end. Your buddy, Zach, isn’t being possessed, so he wouldn’t have any clue how to get to Sam.” Her heart drops into her stomach, as she’s reminded how in over her head she is. “Look, 90 days in the darkest pits isn’t going to be kind to Sam. Especially if those demons are pissed that he didn’t ‘play his role’ or whatever. Maybe you should just go back to Stanford-”

“Go to Hell.” She spits out. Bobby gives another sigh, the static on the line crackling.

“Look, Jess, it was just a suggestion. Dean-”

“Dean abandoned him, Bobby.” She snarls, anger unfurling in her chest. “I’m not going to do the same. I’m going to find my fiancée.  He saved me, and I won’t abandon him to-” The tears pour out, like they have every time she thinks about what Sam is undergoing, every second of every day. Closing the phone, she walks back to Becky’s room, before dropping her mouth in shock.

* * *

 

By the 3rd year, Sam had given up hope of seeing Jess again. He didn’t even expect for Dean to find him, even though he had more expectation on his hunter brother than his dazed, confused fiancée. Ex-fiancée, he reminded himself. Hopefully Jess was safe in Med School, cutting open cadavers. Maybe she had a new boyfriend, one who can keep her safe. Maybe she had a puppy.

He’d remembered her last birthday that he had spent with her, asking her if she wanted one:

_“But why would we need two?” She asked mischievously, rubbing behind his ear like he was a dog. “I already have the sweetest little puppy to follow me around, named Sam.”_

_“Haha. Blessed are you, Miss Moore, to grace me with your wit.” She smiled and kissed him on the nose, making him show his dimples. “I love you, Jess.”_

_“Love you, too, Puppy.”_

He’s now approaching 93 billion years in Hell. The memories he has of his life are less than .01% of his existence, and the memories of Stanford even fewer. Anyone who could possibly know if Jess ever became the cardiovascular surgeon she always wanted to be (“I want to fix hearts.” She’d insisted firmly, giving him a kiss on the nose. “Starting with yours, you big lug.”), or if Becky ever became the first female president of the United States, or if Zach and his girlfriend ever married, or if Luis ever found out what “no more shots” meant is long dead at this point, just like his friends are.

Death is too kind for a thing like him, however. Because in the end, he had hurt everyone, let everyone down. Jess, Brady, Dean, his Mom….

He deserves every second that his body is torn apart. Every minute that the flames scorch down to his bones. Every hour that the demons waste by using his flesh for their carnal desires.

It’s funny. On earth, the only two people who he’d ever been with were Jess and Brady. It had been months before Brady could persuade him into it, because of his own fears of intimacy. When he’d relented, he almost regretted making Brady wait that long, because the feeling of being filled to the brim by someone who loved him and desired him as much as he did them was euphoric in almost every way. He’d actually cried during the first time, and had to explain to Brady that it didn’t hurt, he was just amazed by how much love he felt.

_“God, you’re such a girl,” Brady teased, giving his trademark smile and kissing Sam on the cheek, wiping off his tears. He’d then pulled the other boy’s legs higher over his shoulders, pushing himself further inward and blinding Sam with the ecstasy being caused via his prostate._

_Sam had already finished, but Brady’s gentle movements and deliberate strokes had brought him to the edge again before the blond had finally poured out into him. Afterward, regardless of the stickiness, they’d lain there and cuddled softly, hoping for all the world that they could stay like this for all eternity._

Jess was more or less the same. Except, she had it worse, because not only was Sam afraid of intimacy, but he was afraid of hurting her. He had accepted his role as submissive with Brady, but with a girl there wasn’t much option. Not to mention, he was afraid that if he had sex with her, she would become just like Brady had. Leering, unkind, spiraling. She’d abandon him for drugs, or perhaps more attractive people to bring to her bed. He didn’t exactly explain the specifics of whom he’d slept with before, because telling your girlfriend the only way you’ve had sex is on her end would not be the most desirable way to assert your sexual interest in women (well, her in particular), but she just smiled.

_“I can’t promise that I won’t leave you,” She confessed. “Though I hope when that day happens the Doctor appears in his Tardis and beats the crap out of me, because then I’ve clearly gone mad.”_

_“You’re such a dork.” He snorted, leaning against her shoulder. She gave a smile, similar to Brady’s before he’d gone bad, before kissing him deeply._

_“And you’re a nerd. And together, we’ll have tons of sexy_ Nork _moments.”_

His size had been problematic. Even though Brady had made him well aware that he should be the one topping, he had never actually used that part of his anatomy during their sessions. That spot Brady hit over and over was just too good to give up, and his boyfriend had not been the most comfortable with being on the receiving end, especially due to Sam’s girth.

Jess, however, had had no problem:

_They had made it to the bed, Sam on top of Jess, and were currently having a passionate round of groping and making out. Jess had already been completely stripped (her actions, not his. Even though he had stared for a good five minutes, only to be met with a sarcastic comment from Jess about how if he liked what he saw, he should probably do something about it, otherwise seeing was all that they would be doing that night.), and Sam was left only in his boxers._

_He was briefly aware of her hand slipping under the waistband of his underwear, before a pause. Jess had frozen on purpose, to make sure Sam met her eyes. So that she could confirm that he was giving consent, that he was ready to be bare to the world._

_God, his girlfriend was so awesome._

_He’d given a nod, and began an attack on her neck while she pulled the fabric down his legs, and pausing again to examine him._

_There was an awkward silence, with Sam watching his girlfriend intently, waiting for a reaction, while the aforementioned girlfriend was staring down at her boyfriend’s recently uncovered midriff._

_Sam knew from the comments Brady had made that, proportionally, he was the same horizontally as he was vertically. That is to say, long, muscled, and imposing._

_“It’s fine if you just….you know.” He said lamely. God, he was guilting her into this. He was the asshole feminists taught about in discussions about consent and rape and coercion. Should’ve known that something would ruin the good that they’d been having sooner or later. He was actually kind of surprised that it came this late in the game. Similar to how he’d been surprised that he’d made it so far with Brady, before that all went south._

_He should leave, right? Saying that it was ‘fine’ and remaining on top of her was kind of sending mixed messages._

_His thoughts were abruptly interrupted, as he ended up pinned beneath Jess, who wore an expression of pure lust. Sam felt very confused. Was this how someone stopped an initiation for sex? He watched, still wearing a frown of misunderstanding, as Jess stood over him._

_As she stooped lower, blond tuft between her legs rapidly approaching Sam’s….well…_ flesh _, he recognized in shock that Jess wasn’t walking out. Pretty darn far from it._

_As she sank onto him, he had moaned, almost as high-pitched as possible for his voice range. This….this was just intoxicating. Warmth spreading around him, wet, comforting, embracing. He could relax into this._

_In fact, he did, shuddering softly and wrapping his arms around Jess as she went to work._

In hell, there had not been any such intimacy and comfort. Sam wasn’t sure why he was so surprised. After all, demons did not ask consent when entering a human when they needed a meatsuit. So why should this be any different?

There were a few individual cases of demons asking for his permission. Beleth. Kinaidia. Na’amah. Jackson. Cecily. Of course, they had not really cared about him. They were just offering comforts of flesh because they wanted to cover their self-interest.

No, the only two demons who care about him are Meg and Ruby. They were originally pawns, like Cecily and Kinaida, sent by the higher-up demons to make him malleable to Hell’s will. Of course, for some odd reason, he had aroused the deepest memories of their souls. The memories of being human, which had previously been buried and wrapped up in everything evil and ugly about them. Yes, somehow, Meg and Ruby saw reflections of their former selves in Sam, and they ended up adopting him as a kind of younger brother. And, like Dean had before Sam decided to go to Stanford, they stick up for him, in the face of more terrifying, more powerful demons.

They, in fact, are the ones who worked around to grant him a respite. It had been fairly recent, around 82 billion years after he entered Hell. The other demons, especially Azazel, had been dubious of letting the traitor have a break from his torment, much less for as long as Ruby and Meg were asking. However, the two demonesses had successfully convinced them of turning away from Sam, for a brief 10 million years, and letting him roam Hell, so he can learn, and have his mind expanded, and become the weapon and follower of Azazel, and Hell, and _Him_.

He knew his “sisters” had been lying through their teeth, or at least hoping with all their (flayed and tortured) souls that Sam proves them wrong, because they’ve known him long enough to know he would never become a tool to Azazel, or to Hell.

He spent all 10 million of those years of respite in the vast Archives of Hell, despite the teasing of Meg and Ruby of how _nerdy_ he was. He didn’t care, even though he was tempted to point out that by this time nerdy was an ancient, obsolete adjective. As soon as he had the first book (well, according to Meg, it only appeared as a book to Sam, because his human senses could only perceive it in certain perspectives, while in reality it was more like an energetic manifestation or embodiment of knowledge), he was hooked. He became the Scholar he had been at Stanford. Of course, he didn’t need to read the “books”, because, like Meg said, they weren’t really books. He just needed to hold them, and the knowledge contained in them would literally transfer over into his mind, embedded in his soul.

Throughout the course of the 10 million years (far longer than the length of time humans had existed when he left Earth), Sam had devoured all the knowledge Hell’s Archives had to offer. By the time his respite was over, he had learned and perfected every spell, curse, and ritual in Hell’s arsenal. He’d memorized over and over the Hierarchy of Hell, and the history of all it’s major demons, including Lilith, Alastair, Abaddon, Azazel, and Astaroth. All the lore that had ever been formed, and the seed of truth in each and every story, came to light. He learned of Heaven, Purgatory, and every being and beast that roamed the earth, and roamed elsewhere

He’d even found quiet a decent amount of information from human history. Well, he supposed that shouldn’t be so shocking. After all, most demons were originally human. They came from every walk of life, because every walk of life had been filled with humans who murdered falsely in their gods’ names, who butchered their own kind, who had made deals with hell, who siphoned power from hell, so in turn, those humans must have gone to hell.  The information in the Archives pretty much spanned from Adam and Eve to the Bush-Cheney Administration and the War in the Middle East, the name of every slightly important person, the recording of every event or tradition or play or work of art, and the details of every language ever spoken (in every variation of dialect and every step of the transition into another language).

Oddly enough, Sam couldn’t find anything about what happened in the 80 billion or so years after he entered hell, which was highly confusing. After all, how could so much ancient knowledge from humanity’s lost histories be here, and not the information in the age of technology, where even the slightest irrelevancy was preserved forever by social media?

However, almost as soon as it had been granted, his respite had ended, and he was dragged back into torment.

And it never, ever stopped after.

* * *

 

“What the Hell?” Jess exclaims. She originally thinks that she’s standing in front of a mirror, before she realizes that her reflection is smirking, sneering, which definitely does not mirror the look on her own face. Becky’s tied up on her bed, eyes alight with a mixture of confusion and fear at the two Jesses occupying her room.

The false Jess is quicker to act, trying to make a break for it, only for Jess’ almost 3 months’ worth of training to kick in, allowing her to knock the creature to the floor.

“Get off,” Fake-Jess growls, attempting to knock the equally-weighted girl above her off.

“You’re not a demon.” Jess says, confused. Her doppelganger sneers.

“You must be a crap hunter if you don’t know a shapeshifter when you see one.” It spits. Jess feels her eyebrows raise. So Becky wasn’t crazy when she was insisting Zach would’ve had to be in two places at once.

“You killed Zach’s girlfriend, disguised as him.” She concludes. The shapeshifter laughs.

“Masterful deduction, Sherlock.” It tries to shove her off again, but her hunter training allows her to hold the monster down.

“Okay, but you aren’t like Wendigos or Rugaru or Werewolves or Changelings.” Jess says with a grunt. “You didn’t eat Zach’s girlfriend, you just killed her. So what gives?” The creature gives a snarl.

“Maybe I just liked the sounds of her screams.”  It growls. “Maybe I hate that you can all live life, while I suffer.” Jess’ face hardens. She knows maybe Sam would feel slight sympathy, except for incriminating Zach, but this thing was conscious of it’s actions. It was an utter sociopath.

“Maybe.” She concedes, withdrawing the gun strapped to her leg. “But here’s what’s going to happen. You’re going to take on Zach’s form, come with us to where they’re holding him, let them catch you, and then shapeshift into another form.” Her counterpart seems unimpressed.

“And if I don’t?”

“I shoot you with so much silver your previously worthless body will actually have some use in death.” The shapeshifter shrugs.

“Fine. Just take me to the bathroom first. You’re not going to like the shedding.” Jess knows this is probably an attempt to escape, but she’s not that stupid. Even if it is her first rodeo.

After untying a stunned Becky (gun aimed at shapeshifter), she leads the shapeshifter into the bathroom adjacent to Becky’s room (which conveniently has no windows), and locks the door behind them. Her doppelganger smirks, stripping out of it’s clothes and stepping into the bathtub.

“How’s the search for Sam turning out?” It asks, playing with its breasts in a way that’s really disconcerting. Jess almost fumbles with the gun that she’s holding at the creature.

“How do you know?” She demands, pistol shaking slightly. It rolls its eyes.

“I can see everything in your head, genius. Every thought, every memory. Mine.” The shapeshifter drawls, giving a sickening smirk, cocking its head. “It’s poetic, really: He leaves the life of hunting and starts shacking up with you, gets taken to save your sorry ass, and then you become the exact thing he was running away from.” Jess pauses for a minute, before cocking the gun. “You really want to shoot, Jess? Your friend Zach’ll have no way to be proven innocent.”

“If you have access to my thoughts, you know I wasn’t here to save Zach.” The shifter snorts, still examining its own form.

“Right. You thought he was possessed, like your friend who took Sam. Wanted to break your boyfriend out of hell.”

“Just shift before I put a bullet in you.”

* * *

 

Fifteen minutes later, (with the most nauseous feeling in her stomach), Jess exits Becky’s bathroom containing a bag of the Shapeshifter’s skin, followed by the shapeshifter, now resembling Zach, who is completely naked.

Becky is shaking, and almost shrieks in shock when the extra Jess has been replaced by a duplicate of her currently imprisoned brother. Jess and the Shapeshifter dress, her into the plain black suit she brought, it into the clothing it had been wearing, stolen clothes of Zach’s, still covered in his girlfriend’s drying blood.

“Becky, you’re going to stay here.” Jess orders, taking the shapeshifter and cuffing it, gun pressed against its head. The Warren girl almost protests, but a glare from her friend shuts her up. Jess and the shapeshifter make their way downstairs and get into Becky’s borrowed car, driving down to the holding center where Zach is being held.

“Ruthlessly tactful of you.” The shapeshifter comments. “You drop everything to save Sam, but your other friends are a careless afterthought. Not even done with your first case and you’re already thinking like a hunter.”

“I’ll still kill you if you don’t shut up.” She growls, grip on the wheel hardening. The monster gives a huff.

“You might want to try showing more sympathy. Us ‘monsters’ are not what you think.” She rolls her eyes.

“Yes, I’m well aware of ethics and all your bullshit. I did attend Stanford.” She bites back, as they pull off the highway. Fake-Zach sneers.

“ ‘Dja learn about the value of the soul, or the distinguishing traits between monsters and humans at Stanford, Jess?” It bites back. “All Zach here remembers is a writing seminar, several French classes with a hot T.A, and long lists of economics and business courses.” She’s tempted to point out that the defining trait on Zach’s application was probably his Legacy Status and his family’s ability to pay full tuition, but decides against it.

“You killed Zach’s girlfriend just for your own pleasure, and resentment of other people getting to live normal lives.” Jess says evenly. “By human standards, that’s a serial killer.”

“I’m not human.”

“Pretty damn close, in comparison to other beings. You have no hunger compelling you, and you can almost completely resemble. I’m sure you’re not even the only shapeshifter. You could try forming your own colony or whatever.” The serial killer snorts.

“Pretty damn opportunistic for a hunter.”

“That’s because I actually am hunting for something.” She counters. The shapeshifter raises an eyebrow, confused.

“Meaning?”

“From what I hear, most hunters get in the gig the hard way. They train ruthlessly for revenge, and once they finish, they never really stop. They just travel around aimlessly, looking for any intelligent life that isn’t grade-A human, gank it, and live out the rest of their life that way. That’s not hunting, that’s genocide. Serial murder.”

“And you’re so much better?”

“I’m actively looking for a way to get Sam back. I’m _hunting_ for a way to save my boyfriend. The minute he’s out of Hell, I’ll drop everything to look after him. I’ll do cases to save people from things like demons, or ghosts. Their time on this Earth is finished. Everything else is not my problem, unless the cost of human life is more than it needs to be.”

“Don’t really care about saving your fellow man, eh?” The shapeshifter asks with a grin, as they pull up to the police station’s parking lot.

“We can’t save humans from themselves. We really have no right to judge others for doing so. They live on this earth just as much as humans do, they have the same claim to it.”

“Even those who kill people?” Fake-Zach challenges, as she gets out of the car. Crossing to the other side to open the door for the cuffed creature, she shrugs.

“Like I said, it’s your earth as much as it is our Earth. We kill our own kind for stupider reasons, so we’re in no position to judge. Other things have a need to eat, and that, unfortunately, sometimes means humans. We’re in a surplus, and keeping more of us is going to destroy the world. The only modern way of keeping the population from bursting forth, apart from Mass Genocide, is letting other creatures have free range.”

“Mmmm. Does that mean you’ll let me go?” Jess snorts.

“No. You killed Zach’s girlfriend for fun, so you fall into the same category as humans who do so. The trash pile.”

When they enter the police station, they cause an uproar. Jess isn’t so shocked about this. A young blond woman who appears barely out of college dressed like a fed entering a police station with a bloodier version of the supposed murderer who is supposed to be locked up in the same police station in tow is bound to cause such a thing. She and the shifter are almost immediately swarmed by a group of policemen, most of whom are paunchy and middle-aged white men.

“What in God’s name is going on here?” A man, who she assumes is the Chief of the SLPD, demands. Wordlessly, she withdraws the only badge she brought on the trip.

“Agent Pankhurst, F.B.I. I’m here with my superior, Agent Willis, who came to interrogate a Zach Warren while I did a little investigating, and I found our little doppelganger here. You should probably take him into questioning” The Chief’s eyes narrow.

“And what was the reasoning for your investigation, Miss Pankhurst?” He asks, because what right does a young blond woman have to swagger into his station and order him around?

“It’s _Agent_ Pankhurst, thank you.  And, I don’t know, maybe because there was a murder and the only possible witness provided a verifiable alibi for the perp?” It’s very cynical, very bitchy, and unlikely to get her very far, but she can’t hold in the irritation she feels, and shooting the shifter will only get Zach stuck in jail.

“And just who the hell do you think you are?”

“An agent of the Federal Bureau of Investigation, trying to solve a murder case. And I’d appreciate it, sir, if you tried to help me in doing so. I doubt the people of St. Louis would be glad to hear that their tax dollars are being spent on a police force that’s quicker to jump at blows to their ego than to the news that they might be holding an innocent man in custody.” The police chief’s face is past red, approaching something that appears to be maroon, but thankfully the other officers react quickly, taking the shifter and leading it away. Wordlessly, she walks after them, silently singing praises when she runs into Bobby.

“Jess?” The man blinks. Jess nods, silently avoiding trying to stare at his comb-over. There’s a damn good reason Bobby always wears baseball caps, even to bed. “The hell are you doing here?”

“No time to explain, Bobby,” She whispers. “Look, do you know a spell to make a shapeshifter shed it’s skin like a mask?” The man’s eyebrows arch.

“Who do I look like to you, girl, Gandalf?”

“Gimli, actually, but that’s beside the point. Look, Zach was with Becky the whole time, the murder was done by a shapeshifter. It tried killing me, and I got to coerce it into shifting into Zach’s form and took it down here.” Bobby gives her an incredulous look.

“You brought a shifter down to the Police Department?” He growls. “Were you dropped on your head as a baby, or were you just born stupid?”

“Zach was going away for murder-”

“Yeah, and now there’s gon’ be nation-wide coverage of a murder committed by the twin he never had. Doctors’ll run thousands of blood-tests and see that he’s a 100% match for Zach, even down to fingerprints and DNA, assuming they don’t rip off his skin. And if that happens, the whole Huntin’ world crashes in on it’s ass, and everyone’s hollerin’ about demons and ghosts and werewolves and rugarus until no one trusts anyone.”

“-Which is why we need a spell on how to shed a shapeshifter’s skin easily, so it looks like a mask.”

“And when they hold down the shifter for questionin’ bout this fancy new technology that imitates anyone?”

“We break it out.” Bobby pauses, sighing.

“I’ll see what I can do.”

* * *

 

Nearly six hours later, they are leading the shifter (now wearing the form of John Winchester, as Jess had planned in her head, which the shifter remembered from it’s time in her form) and a very confused Zach out of the police station. Amazingly, after a long list of calls, the two hunters were able to concoct a modified salve from Tokugawan-era Japan, designed originally to painlessly remove the animal skin off an Obake (another form-changing creature) and turn it into a strange, silken material. After adding in a few flecks of the shapeshifter’s skin (which Jess is so glad she brought in the garbage bag in the trunk), they were able to use it in the interrogation to make the Shapeshifter’s Zach form rip off easily like a silicone mask, to reveal John Winchester.

Thankfully, the stupid misogynistic pricks running the St. Louis P.D don’t question a fellow paunchy middle-aged white man when Bobby informs them that John Winchester is wanted by the F.B.I for the supposed murders of his wife and a slew of other people, and the abduction of his own son. It works out perfectly, of why he would pose as Zach to murder his girlfriend. After all, Zach Warren was a friend of his younger son, Sam Winchester. He was one of those “Stanford brats”, who’d filled his son’s head with lies, convinced him that he was too good for his family. Or, at least, that’s what the Shapeshifter manages to convince the police.

SLPD isn’t even questioning the face-morphing technology, which by all natural means should and does not exist in the modern world. But, Jess supposes the greater Saint Louis area has more pressing criminal matters to attend to than insane middle-aged white veteran serial killers with superhuman technology. After all, there are grocery stores in low-income areas being robbed.

When they get back to the Warren house, it’s nearly midnight. Zach and Bobby go first, with Jess and the shapeshifter (gun to it’s back) bringing up the rear.

Becky, of course, is furious when she meets them at the door.

“You have five minutes to explain what the hell just happened.” She spits, red in the face. Jess shrugged.

“I got Zach out of jail.” She explains lamely. Becky isn’t buying it.

“You’re almost completely unfazed by a carbon copy of yourself bursting into our house, you pin it down with strength that I _know_ you didn’t have six months ago, you’re only confused that this thing was a shapeshifter instead of a demon, and you managed to bring it to the police station, in Zach’s shape.” There’s a silence, as Zach, Bobby and the shifter give the two friends some space. Becky, whose face is viciously maroon, gives a rough exhale. “Talk. Now.” Jess shrugs.

“Not much to tell Becky.” The other girl gives a snort.

“My ass. So, what, you have this whole secret life where you fight things? Crap from mythology?” She shrugs again.

“Well, this is my first actual case.” Becky gives a humorless laugh.

“Thank God this is only your first case. At least you have some level of normality.” Jess holds back a snarl, half-ready to smack her across the face.

“Fine. I came, I fixed the issue, I’m gone. I’ll stop infecting you with my abnormality.” She spits. Becky tenses, before loosening slightly when she sees her friend’s anger.

“Jesus, Jess. I didn’t mean it like that.” She murmurs lamely. “It’s just….you’re down with the weird going on. I mean, dropping out of school and not talking to anyone after Sam got abducted by his crazy psycho family? Sure, I get that, even though it’s unhealthy. But _this_ …” Becky gestures to Bobby, and the shifter-John, and her brother. “God, did Sam even _know_?” The hunter holds in a gasp of something like pain, as the thought of her fiancée fills her.

“Sam’s why I’m here.” An awkward silence fills the room. Bobby has the good graces to interrupt it, giving a sharp cough.

“Well, I’m ‘unna take Man ‘a Many Faces here outside. Give you three a little time to catch up.” And with that, the hunter and the Shapeshifter exit the Warren house, leaving her two friends from Stanford staring at her, while she eyes the floor.

* * *

 

“So….Sam comes from a family of Monster hunters?” Zach asks, voice layered with doubt. Jess laughs.

“I know how it sounds.”

“Yeah, but do you?” He challenges, aggressive. She glares at him.

“I had to find out by having one drag Sam out of our apartment. You really don’t think I know?” She growls. He immediately becomes docile, looking almost ashamed.

“It’s just a little too crazy, Jess.” The older Warren points out. She gives a careless shrug.

“The videos show you coming to Emily’s house at the same time Becky swore you were with her, Zach. You know yourself that you didn’t kill her, and the film shows that you did. Explain another way.” She’s aware that these words are cutting into them, and that they are exhausted by the overwhelming inflow of information, but she ignores it. “Shapeshifters are among the least difficult things to wrap your head around, believe me.”

“So, what else is there?” Becky ventures, unsure. She gives a shrug.

“That’s the problem. New stuff is discovered every year.” She answers. “The main things you run into on a hunt are ghosts, because humans are the main sentient species on earth. Of course, there are all kinds of ghosts: Women in White, Poltergeists, Death Echos, Buruburu, Vengeful Spirits, Violent spirits. Then there’s werewolves. They’re nasty. Ghouls, too. Changelings, Djinn, Rugaru, Wendigo, Skinwalkers, Chupacabras, and Pagan Gods are all fairly wide-spread in America, and then, of course, you have some monsters limited to a territory. Selkies stay in Scotland, Okami stay in Japan, Lamia stay in Greece. The works.”

“What about demons?” Becky asks. Jess freezes. Her friends notice, and the younger Warren tries very quickly to ignore it. “Never mind, Jess, we don’t have to talk about it. It’s fine.” Jess shakes her head.

“No, I’m fine…I’m-really, I’m fine.” She isn’t, of course, but she needs to explain to her friends. “Bobby knows more about demons than anyone else in the Great Plains. He’s taught me everything he knows about hunting, demons in particular. I know a couple exorcisms, how to make a demon reveal themselves, how to identify omens, how salt and iron and holy water burn them. All that stuff.” Zach frowns.

“So, is that why you came here? Demons?” Jess sighs, nodding.

“Yes.”

“Why? Did you think I was possessed?” She nods again. “So you came to help me?” This will probably hurt Zach and Becky, a lot more than she means it to.

“No. I came looking for Sam.” The two siblings look confused, so she rustles up the energy to explain why she’s here. “Sam was taken by a demon. It was supposed to kill me, to push Sam into insanity and drive him on a path to destruction or something. It was a plan that had been in the making since before Sam was even born, apparently. He wasn’t supposed to be in the apartment with me. He was supposed to be off with his brother or something.” Her voice shakes, and God, she can feel the tears already. “He was supposed to wake up and find me pinned to the ceiling, and watch me burn alive.” The two civilians already look sick at the thought. “It was going to send him back into hunting, watching me die like his mom had died. But, he _was_ with me, so he made a deal.”

“A deal?” Becky asks weakly. Jess nods, crying softly. “What….what was it?”

“He goes home with the demons, and they leave me and the rest of his friends alone.” There’s a silence.

“So, do you know where ‘home’ is?” Zach asks, sounding confused. Jess bites her lip, closing her eyes to seal in the tears threatening to spill out.

“Come on, Zach. You’re smart. Even someone who isn’t versed in lore knows that only one place is considered home to demons.” Becky gives a little gasp, dropping the beer that was in her hands, and it shatters on the floor. Wordlessly, Jess gets to her feet and walks to the closet, where she knows the dustpan and broom are.

“How can we help?” The hunter frowns, turning to face her friends.

“Help?” She repeats. They nod. Jess holds back a sigh, moving past them to sweep up the remains of Becky’s broken beer glass. “You can’t. You’re just normal people.”

“You were a normal person 3 months ago, Jess.” Becky points out. The hunter snorts in contempt, desperately wishing to point out that the minute she saw Sam-maybe since the minute she was born, even-it was determined that she wouldn’t be normal, because she was hopelessly in love with him, and the universe had declared Sam Winchester should not be normal, because no one that sweet, that loving, that mischievous, that attractive, that intelligent, and that selfless should also have an easy life.

“Sam went to _Hell_ to save _me_.” She emphasizes strongly, trying to get it through her friends’ heads.

“You wouldn’t be in trouble in the first place if he’d told you the truth about his life.” Zach says with a sigh, and Jess Honest-to-The-God-she-no-longer-believes-in snarls in his face.

“Yeah, cause I would have believed in demons and ghosts and witches without being pinned to the ceiling by one, Zach.” She spits. Seeing him wince slightly, she feels the fight drain out of her (that’s been happening more often than she’d care to admit, she should fix that). “Sam wanted to escape hunting. He wanted to deny that life, and he wanted Stanford, wanted us to be his new start. He’s already going to be destroyed that I became a hunter.” More tears. Damn fucking emotions. Why couldn’t she just be a robot, or a blissfully unaware idiot like her entire family? “He’s never going to forgive himself, and you know he will. He’s never going to forgive himself, because he’s just going to see himself ‘ruining’ my chances of a normal life. I can’t handle having him deal with you two becoming hunters to save him as well.”

“Sucks to suck.” Zach declares, taking the dustbin and pan from her. “He’s not just yours, Jess. Sam Winchester is my friend. He was able to help me in a class that I was taking junior year when he was a freshman, and he looked after Little Becky here when I left Stanford.” He wraps an arm around his sister.

“You can take that ‘Little Becky’ and shove it up your ass, Zach.” Becky says with a snort, before turning to Jess with a soft look. “He _did_ talk me out of dropping out my sophomore year, when Zach had left and I was afraid of failing. Not to mention, he tried including me in everything you guys did, even when people complained about involving ‘Warren 2.0’. Then he stood you up on your second date,” Her mouth curves slightly as Jess chuckles. “Not the best idea, by the way-because I’d gone out and gotten drunk after I caught my dickbag boyfriend cheating on me. He came and found me, and took me back to my room, and tucked me in, and did my homework and everything, and waited till I woke up, and made sure to visit me every day for a _month_ or so after.” She stands a little straighter. “So, yeah, Jess, we’re coming with. You’re going to either have to teach us or watch us fail trying to catch up with you. And-unless I’m getting the wrong impression here-failing at this kind of thing only means one thing.”

Jess is on the floor now, crying into her hands because she doesn’t know how she got surrounded by people like Becky, Zach and Sam, and the stories Becky brought up reminds her how pure and loving her Sam was, and how much she misses him, and because this is just a reminder that every minute burns her entire entity with the knowledge that he is in torture because of her.

The blond Warren sinks next to her friend, pulling her into her arms, putting her head into her breast. Jess remembers when her mother or father or older siblings would do this. However, the memories of what they were comforting her seem laughable now. Not making president of the National Honor Society or Key Club or SGA at her school. Making a 1590 on her SATs instead of the perfect 1600 she wanted. Not getting asked out by David Martin to Prom. Getting rejected by Caltech and Harvard and MIT and Princeton and Yale, and having to settle on the 6th best school in the U.S (according to U.S News and World Report). Coming 3rd in her senior class, and thus not being able to make a speech at graduation.

No, all those paled in comparison to knowing your boyfriend was in hell, suffering every moment, because he wanted to save you. And, considering that this boyfriend was the one who had made Jess realize how shallow she was, and had made her more conscious of things around her, she feels all the more destroyed.

* * *

 

Bobby says nothing as they drive back to Sioux Falls, because the shifter managed to get the slip on him, and now the veteran hunter has a black eye.

“So, where are we headed?” Zach asks, shifting slightly in the truck’s back seat.

“Sioux Falls, South Dakota.” She informs them. “Bobby lives there, and Sam grew up a little there.”

There’s more silence, broken only by the ringing of her cell phone. Because the only calls she’s gotten in the past month are police inquiring whether the FBI were really investigating into whatever small-town accident that had occurred, she adopts her professional tone, picks up the phone, and answers.

“Emmeline Pankhurst, FBI.” There’s static on the other line for a minute.

“Jess? Jessica Moore?” Her eyes widen, and she slams the phone shut as quick as possible.

“Really, Jess?” Becky asks with a laugh. “Emmeline Pankhurst? You just had to go there?”

“Why?” Bobby growls. “She a celebrity?” The Warren girl snorts.

“She was a political activist and led the British Suffragette movement in the late 19th and early 20th centuries, so she’s only a celebrity in the eyes of nerdy historians and feminists.” Bobby shrugs.

“Well, better than other hunters. Winchesters are dumb enough to use rock stars.” He looks to Jess, and frowns when he sees her horror-stricken face. “Jess? Somethin’ wrong?”

“Fuck.” She says, finally, because she can barely breath. “Shit, shit, shit, shit.”

“Who was that?” Zach asked, leaning forward.

“Henriksen.” She says. “The FBI agent handling Sam’s abduction.”

“Okay, and how is that bad?” Becky asks. “I mean, sure, it’s useless, but you’re acting like it’s bad.”

“Yes, Becky, it’s bad.” She growls suddenly, ire rising. “Because an FBI agent just heard me say the fucking _FBI_ pseudonym I’ve been using, and he knows that I’m _not_ an FBI agent.” The car goes silent.

“Balls.” Bobby swears under his breath, slamming a hand on the steering wheel.

“And once he finds the pseudonym, he’ll find that I helped you get out of a sentence.” She supplies, turning back to Zach. “And he’ll realize I’m lying about Sam, and that I pinned the blame on Dean and John, and then they’re gonna think I abducted Sam.”

“Wait, you blamed Dean and John for the abduction?” Bobby demands.

“Yes.” She says evenly. “I asked for Dean’s help and he basically told me tough shit, so, I blamed him.”

“Why not just tell them who actually did it?” The hunter growls. Jess gives a groan of frustration. She knows (you’d have to be oblivious not to) that Dean’s the older man’s favorite. Not that she knows how, nor does she understand why, even after all that Dean’s done, but he’s still Bobby’s favorite, and her mentor will insist to his dying breath that Dean is better than leaving his little brother to rot in Hell, and will protect John Winchester’s obedient little brain-dead soldier to a fault.

“It wasn’t his fault, Bobby. He was possessed.” She argues. “Plus, the demon in him isn’t likely to have left itself be tracked by humans. And Sam will be devastated if he finds out that I basically fed Brady to the dogs, because he’ll see it as him ruining Brady’s future.”

“Wait, what happened with Brady?” Zach inquires. Jess sighs. She doesn’t really want to play the ‘Hey, look how much crap has been happening with your friends and you didn’t even notice’ Game, but Zach and Becky deserve to know.

“He’s been possessed by a demon.” She answers, wincing at the gasps by Zach and Becky. “Since Sophomore year. The demon using him hooked us up, and came to kill me before Sam made a deal to save me, and he disappeared with him.” The silence punctuates, before she adds. “I don’t expect anyone to find him, but if there’s the chance that he comes back, I don’t want to mar his whole future just because he was used.” The car goes quiet for another long period of time.

“Jess….” Becky says slowly. “..Brady’s still at Stanford.” Thank goodness the hunter-in-training isn’t the one driving, otherwise Jess would’ve slammed her foot on the break. As it happens, she turns around so quickly that Bobby gives a yelp of shock, and slams on the break anyways.

“What?” She demands. The younger girl shrugs.

“Brady was gone for maybe a week after you left, and then came back and said he went ‘on a bender’. He got accepted in the business school and everything.” Jess feels her heart harden. This is the chance she’s been waiting for.

“Jess….” Bobby begins, warningly.

It doesn’t matter. She’s going back to Stanford.


	2. Flayed

**Summary for the Chapter:**

> Jess helps out a friend.
> 
> Dean turns his back on family.
> 
> Sam spares his enemies.
> 
> Tyson reminisces about his lover.

**Notes for the Chapter:**

> Sorry this took so long! I've been under so much pressure (ignoring my responsibilities) that I've barely had time to update.
> 
> So, this is longer, and much more packed with action (if, by action, one means crying and exposition)
> 
> I'm introducing a bulk of the early season hunters and villains, like Lilith and Alistair and Rufus and Ellen (etc, etc)
> 
> This, like the last chapter, contains somewhat graphic detail of torture, and implications of molestation and abuse. Please be advised to avoid if you feel this may trigger you.

Victor Henriksen usually is very assured of someone’s criminality, at least when he’s the one interrogating them. He never questions whether some nervous behavior is a tell or simply a tic. He never questions the information given when he actually meets the perp, and they try to persuade him that they’re innocent, really, it’s just they were in the wrong place at the wrong time. He never feels sympathy for the person the evidence points too, whether they’re a Veteran or a thirteen year old girl or the nice old grandmotherly figure who bakes cookies and cakes for all the kids on her block.

Dean Winchester is the exception.

Don’t get him wrong, Victor knows the guy is an ass. He’s cocky, arrogant, thinks he’s above the law for who knows what manner of reasons (Maybe because he’s white, maybe because he’s young, maybe because his Dad served and his mom died and his life seems to have been terrible thus far.) But he does seem truly offended that Victor would accuse him of trying to kill his brother’s girlfriend. He seems broken that his brother’s gone. And he’s furious at Jessica Moore, for apparently lying about Sam’s disappearance.

But Henriksen remembers back to his interview with Jess Moore. It’d been the same interview she’d had with multiple authorities and organizations, after they all made connections to seemingly isolated cases, and developed a theory of the Winchester Patriarch and his firstborn being a pair of serial killers (the youngest Winchester, Sam, being the poor soul who had the misfortune of being born into that family, and who tried to escape it). She’d been shaken, to the core. Incapable of comprehending how this kind of thing could happen to her and her sweet, innocent boyfriend (Victor rarely feels anything when people brought up how they don’t why this happened to _them_ , of all people, but in this case, he truly does). And the things he heard about Sam Winchester, how smart and generous and nice (and withdrawn) he was, had been his motivation for trying extra hard to find Sam (in fact, he’d thought once or twice about maybe offering him FBI training, because someone who had been that shattered as a child, with training on how to kill, who still managed to become a frightfully intelligent, kind and caring young man who deceived all those around him about his past deserves a position at the Bureau). Victor knew, among all things, that Jess Moore was not a liar.

Then, a couple months previous, he caught her masquerading herself as FBI agent Emmeline Pankhurst.

Of course, when he checked the records, there was no Emmeline Pankhurst. A google search proved that the most well-known Emmeline Pankhurst was a Suffragette from Britain in the late 1800s and early 1900s.

Right now, he’s checking a case in Saint Louis that occurred a couple months ago, involving Zach Warren. Not because he was assigned it, but because as far as he was concerned, anyone who knew Sam Winchester is a possible target for John, which would help Victor finish the set of Winchester serial killers, and hopefully locate Sam.

Of course, according to the rather irritated Chief of Saint Louis Police, the supposed murder by Zach Warren of his girlfriend, Emily, was proven to be the work of John Winchester, who was then taken into custody by an older Agent Willis, and a younger, female agent (the exact words of the Chief had been “blonde bitch”) Pankhurst.

A blurry security-cam photo emailed to his computer reveals Zach Warren, John Winchester (flashing  eyes no doubt just a glare from the camera), and the agents Pankhurst and Willis.

And, lo and behold, who should the agent Pankhurst be but a dead ringer for Jess Moore.

Of course, John Winchester never made it to the FBI facility that the Saint Louis PD notified. Neither did agents Willis or Pankhurst. And Zach Warren and his sister are currently in the wind, apparently grieving his girlfriend’s murder.

Maybe Jess Moore isn’t a liar, because John Winchester clearly had something to do with his wife’s death.

She’s just not telling the whole truth.

Henriksen examines the photo again, trying to determine who that unknown fourth person is. He’s paunchy, bearded, middle-aged, and white, with a god-awful comb-over and a suit that looks out of place on him.

He vaguely recalls the Moore family, who he tries from time to time to keep in the loop (not that they actually care about Sam Winchester, because they want their daughter to marry someone _normal_ ) saying that Jess had dropped out of Stanford and is currently in Sioux Falls, South Dakota, with the estranged uncle of Sam Winchester (who evidently knows nothing about the Winchesters’ criminal activities), a man who goes by the name of Robert Singer.

Checking the Sioux Falls Sheriff Department’s website (which is basically just has the number of the department and the main email server they use), he dials the number on his phone.

It picks up on the second ring (Surprising, he notes sarcastically. Cause, you know, Sioux Falls is probably such an exciting place.), a bored voice stating that this is the Sioux Falls Sheriff Deparment, what seems to be the emergency? When he identifies himself as FBI, wishing to speak with the Sheriff, the voice on the line becomes much more nervous, affirming they will connect him to Sheriff Mills immediately.

“Jody Mills, Sioux Fall Sheriff, how can I help you?” A sad-sounding woman answers.

“Hello, Sheriff Mills. I’m special agent Henriksen, with the FBI. I’d just like to ask a few questions.”

“Oh. Oh, sure, of course.” Mills says, immediately becoming more focused.

“I’d like to ask about a Robert Singer?”

“Oh, Bobby?” The woman sounds a little confused, audibly blowing her nose over the phone. “He’s the town drunk, lives in a salvage yard. Pretty much keeps to himself except to get groceries.”

“He doesn’t have any family?”

“No, not until recently.” Sheriff Mills is sounding more puzzled by the minute. “There’s a blond girl who makes his grocery runs for him now. She’s been here about 5 and a half months, apparently shacks up with him. Folks think she’s a mail-order bride, but I don’t think Bobby’d do something like that.”

“Yeah, she’s no bride.” Henriksen says with a chuckle. “Her name’s Jessica Moore. She’s the fiancée of Sam Winchester, one of Bobby’s surrogate nephews. Poor girl’s traumatized after he got abducted right in front of her, and she wants to be around someone else close to Sam for support.” He hears a sigh on the other end of the line.

“Poor thing.” She sympathizes “I _do_ remember a couple’a boys following Singer around a few years ago, back before I was Sheriff. They just stopped coming, so I assume that he’d chased them off or something.” Victor really doesn’t have time for chatter with a small-town sheriff, so he cuts to the chase.

“Look, Sheriff, I’ve emailed a picture to your Department, could you just pull it up for me?” There’s a pause, and the audible sound of a spacebar being clicked (and perhaps it’s just his imagination, but he can hear a little bit of sniffling).

“Wow. Okay, I vaguely remember the older guy in this picture, the one whose eyes are flashing. I think he was the father of the two boys? He was there some of the time when they were visiting. I saw the younger man with a beard and black hair this morning, in fact. At the grocery store, with a blond girl. The girl in the picture is definitely the one I’ve seen around town. And that’s Bobby Singer, though I’ve never seen him in a suit and without his baseball cap, and for good reason. That’s one goddamn awful comb-over.” Victor swears silently. “Agent, what’s this about?”

“I’m not sure, Sheriff Mills. But I might need your help in a few days. I have to pay Jess Moore a visit.”

* * *

Day 165

Bobby protests her returning to Stanford. As do Rebecca and Zach. But when she points out that Brady is the only way to get to Sam, and that finding Brady means knocking the demon out of him, and that she is the only one with the combination of enough training and enough youthful grace (sorry, Bobby) to be able to exorcise him, they grudgingly allow her along.

The plan is simple: invite Brady into Becky’s apartment in the Mirrielees House (thankfully, she rooms with Luis, who loathes Brady-the new Brady, at least- with a passion, and who will probably be out the whole time, ensuring he never sees Jess, Bobby, Zach or the demon), lure him into a devil’s trap on the rug Jess has brought in, Cuff him with devil’s trap handcuffs (Becky’s suggestion, though Jess did not think it would work), and bring him back to Bobby’s (because an exorcism at Stanford in broad daylight would be sure to attract far too much attention).

It almost didn’t work. But, thankfully, they now have Brady bound to a chair beneath the Devil’s Trap in Bobby’s study. Sure, Zach’s arm is broken, Bobby’s mouth is stuffed with gauze, and Becky’s eyes are both blackened, but it worked.

To its credit, the demon in Brady has remained largely unscathed, and doesn’t seem intimidated in the slightest. In fact, unsettlingly, it looks rather like the cat who got the cream (and maybe the canary as well).

“Jess.” It intones, leering at her through Brady’s glittering blue eyes. “Been a while since we saw each other.” The next second, the demon is screaming as Jess dumps a sizeable barrel of Holy Water on it. Smoke pours off Brady’s form, as the demon chuckles. “And look at you. A hunter. Bet Sam would be thrilled.” Jess inhales at the mention of Sam, and Brady is laughing again. “Go ahead, ask. We both know the question, so just ask.”

“How do I get to him?” She breathes. The demon gives a tilt of her friend’s head, amused.

“He’s long gone, Jess. This much time in hell? Even if you were to get him back, he’s more broken then Humpty Dumpty.” It sneers. “Downstairs, he’s kinda like the bong at a Frat Party, if you know what I mean. Gets passed around a lot.” Her teeth clench, and the demon’s eyes glitter even brighter. “Or, more accurately, he’s like the girl who passes out at a Frat Party.”

The next five minutes are spent with Jess screaming at the demon, while Zach, Bobby, and Becky (the former with only his unbroken arm) hold her back to prevent her from running a blade through Brady’s body.

“Just do the exorcism, Jess.” Bobby mumbles through the gauze, as calmly as he can.

“This is the only way to save Sam.” She insists,

“Sam can’t be helped, Jess.” He answers, pushing her back. “The demon ain’t gonna help us, ‘less we cut up Brady real bad. That just wastes a person for someone we don’t know is still alive.” Jess has to call upon all the will in her being to not punch Bobby right in the face.

“I respect you only care about him in conjunction with your favorite Winchester, Bobby, but unlike you, I haven’t given up on Sam.” Punching him in the face would have stung less. She sees the hurt in the man’s eyes, but ignores it. He’s protected fucking _Dean Winchester_ , who basically gave up on his little brother, each step of the way, and has also been less than eager to put every effort forward to save the youngest Winchester. Jess’ll be damned if she lets his influence permeate to Zach and Becky.

“Jess, calm down.” Becky says, draping an arm over her friend’s shoulder. “You said it yourself: Knowing Brady was hurt will destroy Sam. We don’t need that.”

The hunter loosens up, leaning into her younger friend’s touch. In a way, even though she fought it, she’s glad that both the Warrens are present. She’s much less likely to quarrel with them every step of the way, because she knows that they’re as committed to helping Sam as she is. While she’s grateful that Bobby took her in and taught her about hunting and this whole life Sam lived, she’s beginning to trust him less and less every day.

Her thoughts are interrupted by the doorbell ringing. She and Bobby share an inquisitive look.

“Expecting someone?” She asks, bemused. The older hunter gives a shake of his head, frowning.

“Guess we could just gag ‘im and throw him downstairs in the handcuffs.” The hunter suggests. The doorbell rings again, followed by banging on the door.

“Robert Singer!” A voice calls out, one that Jess recognizes. “Open up!”

“Henriksen.” She whispers. The doorbell rings again. Brady giggles.

“Are you going to get that?”

* * *

Thanks to a little favor owed, Deacon, Dad’s old friend from the military, busts Dean out from jail. Of course, he obviously knows that Dean’s not guilty of the crime he’s being held accountable for (at least, not entirely).

He’s on a hunt for what looks like a violent spirit passing through various students and faculty at a local community college in Iowa when he runs into Dad. Of course, the old man is shocked as hell to see Dean, considering they’ve both broken into the library at the college.

“What the hell are you doing here?” John Winchester snarls, light flashing in Dean’s face. “And where’s your brother?”

Dean doesn’t exactly know the answer to give. That he couldn’t find Sam? That Sam was being an uncooperative little brat (not that that would be news)? That Sam had fallen into the hands of some ugly supernatural son of a bitch named Azazel, the selfsame son of a bitch who killed Mom, and that the youngest Winchester was probably dead or worse, and that Dean, Dean who had no use for luck charms and spiritual mumbo jumbo, was actually praying that his pain-in-the-ass-baby-brother was dead, because the alternative was too horrifyingly disgusting to think about?

He chooses the second option. Or, a variation of it, at least.

“Kid dug his heels in.” And got dragged all the way to hell for it, probably.

“Damn it, Dean.” His father grinds out. “You shouldn’t be hunting alone. You need your brother’s help! You should’ve pushed harder!” Actually, pushing too hard was probably the issue in the first place. John Winchester should’ve known that foremost among anyone. After all, it was his pushing that lead Sam to abandon them. _No,_ Dean scolds himself, _Sam abandoned us. Maybe he didn’t deserve to be on the receiving end of this thing Azazel, but he sure as hell should’ve known better than to stick his life out for some girl over his family. What kind of moron makes a deal with a monster for someone they barely know?_

 “Yes, sir.” He nods tersely. Seeming satisfied, John Winchester gestures for his son to follow him. “Any clue what we’re hunting, sir?”

“A demon, I think.” His father says. Dean gives out a snort of derision.

“Demon? Like that chick from The Exorcist?” After the Patriarch gives an affirmative nod, Dean blinks. “Dad, I don’t even think they’re real.”

* * *

“Bobby Singer, this is Agent Henriksen, of the Federal Bureau of Investigation!”

“Shit,” Jess curses, looking around the room as her panic sinks in. “Shit, shit, shit! What are we gonna do?”

“Calm down, Jess.” Bobby orders, stilling her with a hand on her shoulder. “No need to fuss about nothin’, till we know it’s somethin’.”

“He heard me use my alias, Bobby!” Jess hisses, her anger from before flaring. “He knows!”

“Bobby!” A second, female voice calls out. The older hunter freezes.

“Jody.” His voice is halfway between fear and bemusement, but Jess decides to focus on the fear. It’s what she’s currently identifying with, anyway.

“Take him downstairs.” She ordered. “I’ll get the door.” After Bobby, Brady and Zach get about halfway down the stairs to the basement, Jess runs to answer the door.

Henriksen’s waiting there, with a chesnut-haired woman in her thirties garbed in an outfit identifying her as Sheriff Mills.

“Jessica,” The FBI agent intones, a soft smile playing up on his face. “Nice to see you.”

“Agent Henriksen,” She says, eyes going wide to convince them that she didn’t know why they were at the door. “This is such a surprise!” The briefest portion of time passed, before she gave a loud gasp, squeezing the agent’s hand. “Have you heard any news about Sam?” The agent’s face winces, possibly from guilt about having doubts on Jess, or possibly because he hasn’t heard anything about Sam, or possibly because Jess is just squeezing his hand really hard.

“No, I’m sorry, Jess.” He says, prying his hand from her grip. Jess frowns, adopting an air of confusion.

“Why are you here, then?” She asks. The agent and the sheriff share a look of discomfort.

“Is Bobby Singer here?” The sheriff finally inquires. Her voice is noticeably congested and hoarse, as if she’s been doing a lot of crying lately. There are circles under her eyes, and now that Jess takes more notice of her, she observes that the woman seems very thin, and that areas of her hair appear sparse or gray.

“He’s just on the property somewhere.” She says after a minute, giving her best fake smile-not an obviously fake smile, but a genuine, comforting one. She opens the door wider, allowing them to enter. “If you don’t mind waiting for a second in the living room, I’ll get him.”

The minute the pair of them are seated, Jess double-locks all the entrances to the study. She then quickly paces to the downstairs bathroom to retrieve from the drug cabinet the small item she’d prepared for Brady’s interrogation, and then swiftly makes her way out the front, and runs as fast as she can into the garage to enter the basement through the door that links them.

Her fellow hunters have gagged Brady, and have him in a chair braced against the iron door that leads to Bobby’s hidden Panic Room. Immediately taking notice of her, the three other hunters back away and let her approach Brady. The demon sneers through its gag, clearly attempting to compensate for the lack of snide or taunting comments it can make.

“I’ve stalled them as long as I can, Bobby, but you’re going to need to go up and talk with them.” She says to her mentor. The scholar pauses, clearly uncomfortable with the prospect of leaving Jess with Brady.

“Just remember what the goal is, Girl.” He says gruffly. Jess feels the anger flare up, and resists to point out that they clearly have two vastly different goals, and instead just nods. The hunter makes his ways up the stairs. The minute the door closes behind him, Jess turns back to the demon and smiles.

“So, you going to do the exorcism?” Zach asks, his voice somewhat shaky. Jess shakes her head.

“Nope.” Nearing the demon, she withdraws the item she took from the drug cabinet- a single eyedropper.

“Jess,” Becky warns, as the older girl tilts the demon’s head back. “Remember what Bobby said-”

“Bobby doesn’t have the same goal as we do.” She spits. There it is again, that anger. “Do you think Brady would want us to exorcise him before we find out how to save Sam? Do you think he would rather us put him first?” Neither Warren rises to the challenge. Jess turns back to the demon, and forced one of his eyes wide open. Taking the eyedropper, she squirts about half of the contents onto the wide blue eye belonging to Brady. The demon shrieks through the gag, as smoke pours off its body.

“Jesus Christ,” Murmurs Zach. “Holy Water in an eyedropper? Pretty ruthless, Jess.”

Even though she’s positive that it’s meant as a critique or chastisement, she gives a Cheshire-like smile in response, and shrugs.

“Majoring in Human Biology had to be good for something.” She answers. “I was thinking of injecting it into the bloodstream, but that would destroy a good amount of Brady’s cells as well.” Moving to the other eye, she repeats the technique with the remaining Holy Water.

Becky blinks.

“Well thank God you haven’t completely gone off the rails.” She quips. “Goddamn, Jess, do you even hear yourself?” Jess turns to face the girl, a cold look of anger on her face.

“Well, there’s no tortured souls screaming in pain for all eternity _here_ , so yes, I do hear myself, Becky.” She says coldly.

“You’re ready to torture Brady, directly disobey the guy who taught you everything about hunting, and for what?” The younger girl demands. “Hell, you’re so busy worrying about what Brady wants, but you never ask if this is what Sam wants.” Almost immediately, Becky cuts herself off, realizing she’s crossed a line. Jess silently turns around to face the girl.

“A couple things, Becky, before you make yourself out to be a _complete_ idiot.” She intones, barely above a whisper. “First, I’m torturing the _demon_ that _possessed_ Brady. The one who ruined Brady’s life, manipulated Sam and I, was about ready to kill me, and who dragged Sam into hell. Secondly, Bobby has been in this life for a long time, and only joined it after a demon possessed his wife and he accidentally killed her, thinking it would stop the demon. This is a bit too close to home for him. Thirdly, he’s already resigned to the fact that Sam can’t be helped, simply because it’s too difficult for him. If he doesn’t want to be involved with this, then we won’t bother him. Fourth, and most importantly-” She holds up a finger, silencing both Warrens as they begin to speak up. “Don’t ever, ever, bring Sam into this. Do you think he’d rather be in hell then here, Becky? Do you think torturing the demon that put him there, who helped manipulate him like a puppet, is something that he’d actually be concerned about? Because, If you do, and if you’re finding yourself on Bobby’s side of the argument –” She turns back to Brady. “You can just go back to St. Louis, and forget about Sam.”

There’s silence for a few minutes, with nothing but Brady’s muffled screams as Jess dumps a bucket of Holy Water on him, the liquid seeping into the crevices of his clothes.

“Jess,” Becky finally says, voice shaking. “I know you’re mad, Jess, and desperate, but please try to understand. Brady was your friend before you even knew Sam. Would you really be okay with hurting him?” She doesn’t respond, and continues to move around the room. “Jess.” The huntress continues to avoid their gaze, before finding herself held in place by Becky. “Jess.”

Losing Sam has screwed with her, there’s no denying it. She contemplates to how she was before this past November 2nd. Back before the demon in Brady came to kill her, and instead took Sam. That Jess was naïve, sweet. The worst she could do to a friend was punch them, and the crime would only be as severe as a very lame pun.

And Sam himself, with enough warmth in his heart to ignite several suns, had perhaps caused the change. The feelings she had around him, had every morning she had woken up in bed to feel the heat of his body, had been replaced and frozen over. Maybe, she thinks, that’s what the absence of Sam does to people. It makes them cold and uncaring to life in general. It would certainly explain why Dean Winchester had acted the way he did when he broke into their apartment building, why he shut her out when she asked for his help.

Her stomach twists. _How would Sam feel,_ she wonders, _if he could see what I’m like now_.

There’s more silence, the three of them standing there.

Then, they hear the gun cock.

* * *

“So, we caught the demon.” Dean wheezes, nodding to the snarling monster stuck beneath the Devil’s Trap they’d drawn on the ceiling of the abandoned warehouse. Of course, it got a couple hits on Dean before he lured it into the trap. John didn’t get it as bad, but of course he has more experience. “What do we do now?”

“Exorcism.” John grunts. “Just have to pray Bobby Singer didn’t screw with me and give me a faulty one.” Dean doubts that Bobby would give anyone the wrong methods to knock a demon back to where it belongs, no matter how he may feel about John.

“Okay. Do we need anything?” The young hunter asks.

“Just the incantation.” His father says, pulling out an old parchment paper from his breast pocket. “But I’m just gonna ask our friend here a few questions, first.” At this, John squats down in front of the demon, extending his hand to Dean. “Holy Water.”

Dean passes it, without hesitation. Why would he? It’s Dad. Dad knows his stuff.

The Demon hisses when it gets sloshed with the stuff, smoke sizzling off its form. Dean can’t help but worry a bit that the poor bastard being possessed might feel the pain, too.

“Are you sure that won’t harm –”

“Holy water doesn’t harm the body, boy. Just the demon inside.” John explains. Focusing on the demon, he leans in. “Now, I just have a few questions. Answer them quick, and this will be as painless as possible. Clear?”

“Bite me.” The thing snarls, eyes flashing black. A healthy dosage of Holy water reduces it to a screaming mess.

“Are. We. Clear?” The older hunter asks again, firmly as possible. Snarling, the demon props itself up from within its prison, and gives a stiff nod. “Alright, then. First off, what’s your name-your real one?” The demon, who currently is a muscled dude in his thirties, quirks an eyebrow.

“Been awhile since anyone’s asked.” It says. “Funny how humans always assume that when you give a name, it’s your real one.”

“No time wasting. Just give me a name so I can write record it.”

“Honestly, I don’t really remember. Been so long since I was human…”

“Wait, you were human?” Dean asks in disbelief. The demon nods.

“Most demons start out that way.” It says plainly, before giving John the side-eye. “Like I said, I don’t remember my real name. The one I use in conversation with my other demon pals is Tom.”

“Tom the demon?” The younger Winchester snorts. “What, d’ya play football with the Patriots?” Tom gives a little chuckle.

“I got ten others which you don’t have the brains to pronounce. Figured I’d go easy.”

“Enough chatter.” John orders. “Now, where’s Yellow Eyes?” The demon pauses for a minute.

“Who?” It asks innocently. Almost immediately, it’s sloshed in holy water and snarling viciously.

“No games.” John orders. “I need to find out all possible locations of the demon with the yellow eyes.”

“Don’t know who you’re talking about.” Tom says, doe-eyed confusion on a borrowed face. Dean’s dad gives a growl of frustration, dumping another splash of Holy Water on it. A glint reveals that the older hunter has already pulled out a knife. The demon’s not too impressed. “Pretty. Iron, I suppose?”

“You’re goddamn fucking right.” The Winchester Patriarch says with a growl that sends chills down Dean’s spine. “Won’t exactly tickle, will it?”

“Sir –” Dean begins to protest. Is John really suggesting…?

“Quiet.”

“No.” The demon admits, nodding its head. “But the only scars that’ll last are the ones on my meat. Hurting humans – not really a hunter’s forte, is it?” There’s a pause, and for a brief moment, Dean hopes that his father isn’t seriously considering this.

“If it gets me to Yellow Eyes….” John says with a shrug. Reaching through the devil’s trap, he presses the knife against Tom’s skin. Sizzling, it causes the demon to give a shriek of pain.

“Go to hell!” The demon snarls, forcing itself towards John’s face. The hunter lifts the knife from the demon’s skin, before forcing it straight into Tom’s chest. The guy – no, _demon_ – gurgles blood and shrieks in pain. Dean looks in panic to his father, but the expression on John Winchester’s face lacks any empathy.

“Dad –!” Acting immediately, Dean pulls the knife away from his father, accidentally scraping the man in the process. The Winchester Patriarch shouts in pain, glaring at his son.

“Dammnit, Dean,” John spits. “If you can’t man up, then just go wait –”

A round of hideous, pained laughter silences John. Both the Winchesters look to the demon, as blood gurgling from its host’s mouth paints the teeth red in a macabre smile. Tom quirks an eyebrow.

“Dean.” It repeats, humor competing with pain in its borrowed voice. “Not Dean _Winchester_ , surely?” The look on Dean’s face must answer the question, because it grins wider. “That must mean –” Tom’s head tilts to John Winchester. “Daddy Winchester!” Tom laughs again, coughing on his blood. “Boy, have I been waiting to meet you two.”

“How do you know my name, you freak?” Dean snarls suddenly, impulsively placing the knife against the demon’s throat. Tom’s reddened teeth flash once more, eyelids flickering black.

“Little brother’s been begging for you.” The demon croons, leaning forward to stare at Dean. Dean feels his blood run cold.

“Sammy?” He whispers. The demon nods. “Where is he?” Dean asks, just as weakly as before. Tom smirks.

“Essentially where you told him to go when he ‘deserted’ you, Big Brother – _Hell_.” Its eyes flash. “He screams your name, begs for your help.” The demon’s gaze flicks to John. “Not you – he either hates you or thinks you don’t care about him.” The demon’s eyes trail back to Dean. “But you……” It shrugs. “He calls a lot of names. His girl’s…… his _boy’s_ ……..Singer’s, too………but the one he’s the most hopeful for is you.”

“What are you doing to him?!” Dean growls, hands shaking. Tom’s face is glittering with joy.

“It’s easier to list what we haven’t already done to him. He breaks so easily, and breaking him even more is where the fun is at.” Dean gives a snarl of rage. Tom chuckles.

And then Tom screams, repeatedly, because Dean nabs the knife from his father and stabs him up and down his body.

“WHAT ARE YOU DOING TO HIM?!” Dean roars. A corner of his mind reminds him that he should feel guilty, that the state he’s left the poor bastard Tom’s using will probably mean that he won’t survive, but all he can feel right now is pure anger and hate pounding through his blood. John has to pull Dean off of the demon, which isn’t easy to do considering how much of a vice Dean has on him. The demon hawks up about a gallon of blood, snickering and laughing the whole time. “I’M GONNA FUCKING KILL YOU!!!!!!!”

“Dean, get your ass outside.” John orders. Dean looks to his dad in disbelief.

“You’re kidding, right? They’re fucking torturing Sam!” The elder Winchester shoots a glare that would make any vengeful spirit scared.

“I heard. Now follow your orders, and get your ass outside.”

“Dad, THEY’RE TOR – ” Dean’s cut off as John Winchester grabs him by the collar and hauls him forth.

“Car, boy. Now.” And with that, Dean feels the fight drain out of him, and he obeys. As Dad begins to recite the exorcism, he is 100 percent conscious of what he is doing. He’s walking away from finding out what is going on with Sam.

He’s turning his back on his brother.

* * *

At the sound of the safety being turned off, all three of them turn around to see Agent Henriksen holding a firearm at them. Beside him is Bobby, handcuffed, being held in place by the Sheriff, Mills.

“Step away from the man, Miss Moore.” The Federal Agent says. While Becky and Zach do so immediately, Jess persists, spreading her feet to shield Brady from Henriksen.

“Agent Henriksen –” Jess begins, but she stops herself from answering. What exactly is she going to say to this man? How it isn’t what it looks like? How Jess isn’t torturing her closest friend? How she hasn’t been impersonating an FBI agent?

“Move aside, Jess.” Sheriff Mills says. “Nobody has to be hurt.” Jess almost laughs at that, because Sheriff Mills has no idea how many people have already been hurt.

“I can’t.” Because the minute she steps aside, they’ll uncuff Brady. And once Brady’s free of the Devil’s Snare Handcuffs, the demon in him will slaughter them all in a heartbeat.

“Please help me!” The demon screams, giving what is in Jess’ opinion an award winning performance. Of course, it also makes her want to stab him roughly thirty times.

She makes the mistake of glaring at the demon for a second.

And in the next, she’s on the floor, watching as Agent Henriksen and Sheriff Mills rush to undo the handcuffs.

“You okay, son?” The woman asks, wrapping an arm around Brady. Her friend gives a choked sob, nodding his head as if in pain. Then, rather abruptly, he gives a snide laugh, shaking his head.

“You know,” He says, looking up to meet Sheriff Mills in the eye. “You really should’ve listened to Jess.”

In the next second, both the Sheriff and the Federal agent are on their knees, choking on their own blood. Jumping into action, Bobby begins reciting the exorcism.

“ _Exorcizamus te, Omnis Immundus Spiritus –_ ” Brady’s features twinge, and his eyes flicker black. Directing his attention to the hunter, he gives a lazy flick of his finger, and the chair he was previously seated in goes flying to strike Jess’ mentor in the head. Another flick sends Becky and Zach flying into opposite walls.

The demon’s eyes shift towards Jessica, giving a soft smile.

“Hiya, Jess.” He says, stepping forward. Stumbling to her feet, she backs against the wall, her heart pounding out of her chest. Sensing her fear, Brady cocks his head to one side. “You know, now that I think about it, the last time we were in the same room, we were in the middle of something.”

She’s not near any iron, or holy water. She stupidly used all of it to torture Brady, because she didn’t anticipate him getting out. The demon realizes this, and gives a hearty laugh.

“Where were we?” He says, eyes flickering black. “Oh, right. You were on the ceiling, bleeding out.” Brady holds his hand out towards her. Immediately, Jess closes her eyes, waiting for the pain of her stomach being sliced open, waiting for the force of being pushed against the wall, onto the ceiling.

It never comes. Cracking an eye open, Jess sees Brady frowning in confusion, hand still outstretched. He forces it outward, again. Still, nothing happens.

“Impossible.” Brady surges forward, glaring at Jess. “How are you doing this?” He tilts his head. “You aren’t using demon blood.” Jess is too shocked for words, unsure if she is understanding the situation correctly. There’s a long pause. Henriksen and Mills are still gurgling on their blood, and Bobby, Becky and Zach are all in various states of semi-consciousness. And Jess is still confused and lost, looking at the demon that is using her friend, watching it mull over.

“The Deal.” Brady whispers, suddenly paling. The confusion on his face cedes to horror, as he begins to back away from Jess. Jess’ brains try to make sense of what Brady’s saying. Then, her memory refers back to the night Sam was taken, and a laugh escapes her.

_Jess and Tyson are given immunity from any supernatural harm._

That was the first thing Sam had demanded of Brady. Of course, perhaps the demon was not trying to actually make a deal, had not been intending to make a deal. But it had been made, sealed with a kiss just like Bobby said all demon deals had to be. She’d never actually considered that the deal Sam had made would be valid, and neither had Bobby.

But now that she thought of it, she’d remained remarkably unscathed for all the hunts she’d been on. The shapeshifter from St. Louis had put up a fight, but possessed none of the inhuman strength Bobby told her to associate with them. The ghosts she’d encountered on the salt-and-burns that Bobby assigned to both her and the Warrens for training had never gotten the chance to toss her through the air. And even before, when they’d trapped Brady at Stanford, he hadn’t harmed her like he had the others.

“Inconvenient when you can’t use your mojo, isn’t it?” She sneers, approaching the demon. “Should have thought before making a deal with Sam.” The demon’s terrified now, using Brady’s blue eyes to express his utter fear.

“Please.” He begs, backing away from her. “Don’t send me back. They’ll torture me when they realize what I’ve done. I’ll leave Ken Doll here, let you have him back, just don’t exorcise me.” She pauses. This is the time to interrogate the demon, while she has the upper hand. It’s not going to risk harming the others, in fear of Jess banishing it back to hell.

“Why have you been in Brady so long?” The demon winces, looking fearful.

“Azazel told me that my job was to watch Sam. At first, I thought my job was going to be to turn him into a little junkie, or maybe just stay in Brady until ordered me to kill him, so Sam would have a reason to start hunting again, for revenge. Instead, he just had me hook you two up, so he could have me kill you.” Jess almost throws up. She and Sam had been purposefully brought together, so she could die. She had been intended to be a pawn, meant to be sacrificed.

“Why did Azazel want Sam?” She demands, moving forward. The demon looks at her incredulously.

“Seriously?” It says. “You expect me to just spill?” She nods. “Forget it. That would make me a dead man for sure.” Jess’ shoulders give a shrug.

“Have it your way. _Exorcizamus te –_ ”

“Wait, wait!” Brady pleads, eyes wide with fear. She stops the exorcism, gesturing for him to go on. “The Winchesters have been the center of a plan that’s been going on for millennia.” Jess frowns. She had heard Brady mention a ‘plan’ the night he took Sam, but she’d barely paid attention.

“What plan?” When the demon stays silent, she opens her mouth wide, readying to spill the exorcism.

“The Apocalypse! Sam was supposed to bring the Apocalypse!” Jess’ heart stops. The demon continues. “Sam and his brother are descended from two families that have long been involved in the supernatural – the Campbells and the Winchesters. Their Mom was the last in a long line of hunters, and their Dad’s Dad was the last of a line of scholars of hidden knowledge. What neither family knew is that they descend from ancient lines.”

“How ancient?” She asks, her curiosity getting the better of her.

“The Winchesters are descended from Cain. The Campbells were descended from his younger brother, Abel.” Jess blinks.

“ _The_ Cain and Abel.” The demon nods, frantic for her to understand. “Like, from the Bible.”

“Yes. So, you mix the two together, make the young man unaware of his heritage and history and the girl just dying to get away from the hunting life fall in love.  Heaven took care of that.” Jess opens her mouth at the mention of Heaven, but shuts it quickly. Not until she’s heard more. “Azazel slaughters Mary’s hunter parents and John when they were still dating, forced Mary to make a deal to bring her boyfriend back to life and told her he’d come to collect in ten years’ time. With her parents dead and her boyfriend resurrected, Mary left the hunting life, married John, and lived happily ever after.” It makes sense now. Azazel was trying to take Mary’s soul, and John had no understanding of why the demon attacked.

“Ten years later, Azazel comes in to six month-old Sammy’s room, and makes good on his deal.” Jess’ heart stops. The shock shows on her face, because Brady gives a sadistic grin. “Mary should’ve had the brains to ask Azazel what he was going to collect in 10 years. Anyways, he drips blood into Sam’s mouth, forever tainting Sam as an abomination – a human with demonic blood.” Brady shrugs. “He’s not the only one. There’s a few others like him across America – Azazel calls them The Special Children. All of them distant cousins through the line of Abel, all tainted with Azazel’s blood from the time they were six months old, all sold by their unwitting parents ten years before.”

“Why were they made?”

“They were supposed to fight each other, until two remained. Sam and someone else. Sam was going to die by the other person’s hands – except Dean wasn’t going to let that happen.” Jess didn’t even feel the familiar brush of hatred at the mention of the older Winchester. “See, you were supposed to die, and Sam would jump back into hunting for revenge. Dean and Sam would reforge the bound that’s withered away while he was at Stanford, and when Dean saw Sam get murdered by the last remaining Special Child, he would make a demon deal to bring Sam back to life.

“Dean goes to hell, and after endless torture he eventually breaks, starts torturing a couple souls of his own. Being of the line of Cain, and not being tainted like Sam, he fits the label of “Righteous Man”, and breaks the first of the sixty six seals of the Apocalypse. A righteous man spilling blood in Hell.” Clearly nothing but a title, if Dean qualifies and Sam doesn’t, Jess thinks privately.

“The first demon, Lilith, would then be free to break any 58 of the other 599 seals in existence, in any order she pleases. Each one brings us closer to the Apocalypse. Sam, mad with grief and guilt by the fact that Dean’s in hell, starts drinking more demon blood, using his psychic powers to get revenge on Hell. He kills Lilith, thinking he’ll stop the Apocalypse.

“But, Lilith’s death is the final seal, so Sam’s actions only begin the Apocalypse.” The demon smirks. “Chaos, War, Cataclysm, Disaster, Disease, all framed by a final showdown.”

“Between who?”

“Lucifer and Michael, the first two angels of God.”

* * *

“Angels.”

“God, did you really go to Stanford? Yes, angels. The 66 Seals are the Keys to Lucifer’s Cage. The Apocalypse, the end time, is signaled by when Lucifer walks the earth. The end of time literally being when Michael and Lucifer fight.”

“How can angels be real if no Hunter’s heard of them?” Brady shrugs.

“We’re real and half the hunters you meet will swear up and down we don’t exist. But they aren’t the fluffy winged harp-players you envision, Blondie. They’re straight-up dicks. Tossed Lucifer out of Heaven and into the Cage just because he wouldn’t worship humanity like Daddy told him too.”

“So, why did it have to be Sam to break the last seal? Why did Sam need demon blood?”

“The first and last seals need to be undone by the True Vessels of Michael and Lucifer. A pair of brothers, one younger and one older. See, in their real form, angels can’t tangibly harm one another, and they can’t interact on this plane. Kind of like us. Except, angels aren’t a one-size-fits-all like we are. They need someone with a specific gene, otherwise the person they’re using bursts.” Jess’ blood runs cold. “And, being the most powerful, Archangels need someone from an ancient line. But the only ones that can hold the angels in indefinitely are the True Vessels.

“Sam and Dean could both theoretically house either Archangel in longer than anyone else could – the blood of the line of Cain lets them house Michael, and the blood of the line of Abel lets them house Lucifer. But, being the father of demons, Lucifer’s vessel would need some demonic blood, so they aren’t completely human. And Michael would want nothing other than pure grade-A human.”

“How do I get to Sam?” Jess demands. There’s a pause, and the demon shakes its head.

“He’s stuck in Hell. The bosses downstairs? They’re never letting him go.” Jess gives the demon an exhausted glare, ready to spill the exorcism. “Wait, WAIT! I’m telling the truth!”

“There must be some way.” Jess insists, feeling her anger spike. Brady shakes his head, terrified.

“Only demons can get in and out of hell.” The demon explained. “Unless you opened a Devil’s Gate, allowing souls that are still human an escape. But no matter how many souls escape, Azazel and Lilith and the other head honchos aren’t giving Sam an out.”

Jess feels her heart break, and closes her eyes. Bobby’d been right. Brady has no method to helping them free Sam. Pain overwhelms her, and she feels the tears begin to slip down her cheeks, counting them.

_One._

_Two._

_Four._

_Ten._

“Tell Azazel I’m going to find him.” She says, opening her eyes to stare at Brady’s. Her pain buried is under anger and hatred now, as she stares into the eyes of her friend, (and apparently her fiancée’s ex), whose life had been ruined by the demon. If she can’t get revenge for Sam, she can get revenge for Tyson.

“Wait!” The demon squawks, backing away. “I told you everything! You can’t just –”

“ _Exorcizamus te, Omnis Immundus Spiritus_ ,” She begins, watching Tyson’s face contort into an expression of pain. “ _Omnis Satanica Potestas, Omnis Incursio Infernalis Adversarii,_ ” The demon snarls, rising to his feet and stalking towards Jess. “ _Omnis Congregatio et Secta Diabolica, Ergo Draco Maledicte, Ut Ecclesiam Tuam Secura,_ ” Fists clenching, the demon sinks to his knees, his expression stricken. “ _Tibi Facias Liberate, Te Rogamus, Audi Nos_!”

Black smoke shoots from Tyson’s mouth, swirling around with angry rage before exiting the cellar through the open window. Immediately, Jess runs towards her friend, to catch him while he’s still on his knees.

“Ty? Ty!” She grabs him tightly, jostling him with the hope that he’s not too far gone. A faint, yet present heartbeat confirms that he isn’t. Their eyes meet, both blue and piercing, before Ty goes slack, unconscious from all the stress catching up to him.

Looking around the basement, she sees the others struggle to their feet, gasping. Agent Henriksen and Sheriff Mills look particularly winded, both wiping the blood from their faces and looking at Tyson with a mixture of fear and concern.

“Care to explain what the hell just happened?” Henriksen asks. Jess gives a weak laugh, hefting her friend’s deadweight form into her lap.

“After a drink or five, maybe.”

* * *

“Demons.” Henriksen says skeptically, tilting back the glass of whiskey Bobby broke out. “You’re saying that demons are responsible for carrying off your boyfriend, and possessing your friend upstairs.”

When everyone was back on their feet, Bobby and Zach carried Tyson into one of the upstairs bedrooms, so he could recover. After that, her mentor busted out all his stores of alcohol, for everyone to ease as best they can what happened today out of their mind. Right now, they’re all in Bobby’s study, seated in various chairs waiting for Jess to recount her story.

“Yeah, I know how it sounds.” Jess says dryly. “Heaven’s in on the plan, too, if that’s any consolation.” It isn’t, really. Even to Bobby, knowing that there’s a whole other group of supernatural beings that are conspiring against saving Sam is anything but a consolation. “It’s been this – plan… one in the making for thousands of years. To manufacture Sam and his brother into causing the Apocalypse, and the end of humanity.”

“Why would Heaven have a part in this?” Sheriff Mills asks, her voice pained. “I get Hell, but Heaven?”

“Don’t know, don’t care.” The woman winces at this, but Jess hardly cares. She’s so numb to the situation, what with the revelation she’s undergone today.

Sam, his family, her, Tyson – they’d all been manipulated and used, to further a stupid fight between two brothers. She was supposed to be a stupid little plot device, to break Sam down. So he would unleash the Devil, so he would break and lose hope. A Heaven that encouraged that, or even allowed that, was no better than Hell.

She’s staring at the book shelf containing Bobby’s lore on demons, not wanting to look anyone in the eye. She still is in far too much shock to comprehend everything.

“We were hooked up, just so I could die.” She finally says. Or, she thinks it’s her, except her voice usually isn’t that weak and broken. It must be her, because Becky gets up from where she’s seated to give her a hug. Jess sinks into her friend’s embrace, forcing her tears back down.

“I still don’t understand why he couldn’t hurt you.” Henriksen says, shifting in his seat. “Something about deals?”

“Demon deals.” Bobby answers. “Usually, to make a demon deal, you have to summon a demon of the crossroads. You make a deal, seal it with a kiss, and they give you what you want. In ten years, they send Hellhounds – demonic pitbulls, really – and drag your soul into Hell.”

“The night Brady took Sam, he was originally going to kill me.” Jess explained, shifting in her chair so Becky could fit with her. “Sam said that if Brady killed me in front of him, Sam wouldn’t do anything that Brady wanted him to do. Sam made him promise that both me and Tyson would be immune to any supernatural harm, and that his friends would be left alone, in exchange for Sam going into Hell.” She shrugs. “I didn’t think that Brady was going to hold up his end of the deal, and apparently he didn’t, either. Until today.”

“But wait,” Becky interrupts, frowning. “Emily was killed and Zach almost went to prison. Doesn’t that violate the deal?” Jess shakes her head.

“Zach’s girlfriend was killed by a shapeshifter. Sam’s deal only asked the demons leave his friends alone. So they wouldn’t get dragged into Hell’s plans.” After a pause, Henriksen leans back.

“And the Winchesters?”

“Dean told me to keep my nose out of hunting and that there was nothing he could do for Sam. The Winchesters were my only other believable option for why Sam had been abducted, and I felt it would be unfair to blame Brady when he’d been possessed.” There was another pause, and Jess inched forward to the FBI agent. “Look, Agent Henriksen, I apologize for lying, but I needed to help Sam, and I didn’t know what else to do in this situation. I know this is out of your depth, and felt that I needed to fix it.” The FBI agent gives a nod, looking back at her.

“This is out of my league, Jessica. Way out.” And, to her surprise, he smiles. “But I made a promise to see it through. So, I think I might need a little bit of training.” There’s an awkward silence, and Jess is trying, fighting not to cry.

“Jody?” Bobby asks. They all turn to the Sheriff, who gives a small smile.

“Well, now that I know you’re more than the town drunk, I think I can’t really let you do all the hard work around Sioux Falls, can I?” She says wryly. Bobby gives a laugh, nodding.

“Guess not.”

* * *

Day 181.

Tyson finally wakes up. After being unconscious for more than two weeks (or, since Sophomore year, depending on the way you looked at it), Jess was unsure if he ever would.

While the Warrens have also been watching over him in shifts, Jess has easily spent double the amount of time both combined have in the room. Because, the more time she’s in here, the less time she has to be out there, with everyone else and the sad pitiful looks they’ve been throwing her. So, she shuts herself in here, reading book after book on demonology and fiddling with the various tubes (stolen by Sheriff Mills from the local hospital).

So, of course, Jess is in his room when it happens. She hears a groan, looking up from the book she’s reading. Tyson’s shifting on the bed, evidently uncomfortable, muttering Sam’s name. Immediately, Jess is on her feet and over him.

“Ty, Ty…” She repeats his name over and over, trying to calm her friend so he doesn’t accidentally tug on any of the tubes controlling his food supply and the contents of his stomach. Tyson’s eyes – bright blue, like hers – finally flicker open. For a few brief seconds, they are content to lazily stare into space. However, they eventually settle on her face.

“Jess.” There’s so much pain and hurt in that voice, Jess barely stops herself from bringing her friend into an embrace. “Sam.” Tyson’s wide awake, his face filled with horror. “Sam,” Jess sees the wetness on his cheeks, and turns away so Tyson doesn’t see her crying, so _she_ doesn’t see _him_ crying.

She has seen Ty cry, once. Sophomore year, right before he left for Thanksgiving and was taken over by the demon, he showed up drunk at her apartment. They were close, sharing many of the same classes as they were both Bio majors. So, she’d let him in, and let him babble about how he needed to tell his family something and he didn’t want them to hate him or be disgusted but he just _had_ to tell them because he couldn’t hide how he felt and he just didn’t know how to tell them.

She knew at the time that Tyson was talking about coming out. When she’d met Sam, and saw how insistent he was about bringing their friend out of his funk, she knew that he was most likely the reason. That Tyson was in love with Sam, as strong as she would come to be, and he’d wanted to admit to his parents how he felt. She’d just figured Brady’s snap during Sophomore year was the result of staying in the closet. All the girls and the booze and the switching of programs from Bio to Business was just an outward reflection of not being able to be honest about who he was.

So, like when she had comforted him the time before Thanksgiving break sophomore year, she finally finds the words.

“Ty, look at me.” She says, trying to steady her voice. Her friend looks up to her, tears streaming down his face, his expression as hopeful as a child’s. She puts a hand on his shoulder. “We’re going to get him. I’m going to find a way to get him.” Her friend shakes his head, a look of pain on his face.

“Jess, it’s all my fault. If I’d just – ”

“Don’t.” She says sternly, sitting on the bed. “Ty, you can’t do this to yourself. You had no way of knowing.” A surge of anger, towards _Sam_ , of all people, runs through her. “Neither of us could have. He never told us anything.” The words sound as bitter as they do in her head, apparently, because Tyson gives a shake of his head.

“Jess, he was _scared_. I knew him since Freshman year, and he was nothing but _scared_. I didn’t understand, but –” He bites his lip, clenching his head. “I should’ve tried harder. I should have _fought_ harder. Jess,” He places his hand on hers, a look of pure fear and sadness on his face. “You don’t know what he’s been through, what they’re doing to him.” Jess’ attention perks, and she almost jumps.

“Wait, have you seen him?” Uneasily, Tyson nods.

“Do you know how to get him?” He shakes his head, crestfallen.

“I’m sorry.” She wants to lash out at Brady, but she knows she’s been doing that too often to allow it willingly.

“Do you want to go downstairs?” Then again, she doesn’t have the emotional capabilities to keep focusing on Sam on Hell if the conversation is not about getting him out. Even if it means Tyson keeping his emotions bottled up.

* * *

By the time they make their way downstairs, Jess is panting. Of course, Ty’s trying his best to help, but it doesn’t change the fact that he’s still weak from 16 days of being in bed and over two years of not actually being in control of his body. And the other fact that even if she’s nearly 6 feet tall, Tyson’s really heavy.

When they finally the downstairs, they make their way into the living room. Jess blinks in surprise when she finds a handful of strangers.

“Jess.” Bobby sounds genuinely surprised to see her. Then again, she has been isolating. He’s standing next to a middle-aged woman with brown hair and a tall black man with a receding hairline. Bobby gives a jerk of his head to Tyson. “See your friend’s awake.”

“Is that how you greet people, Bobby Singer?” The woman says sternly, rushing over to Jess and Tyson. “Good Lord, who taught you manners?” The woman gives a warm smile to the two of them. “Sorry, Honey, I’m Ellen Harvelle. Bobby’s just crap with introductions. What’re your names?”

Jess instantly likes this woman, mainly because of the pure sass she gives Bobby. She also has warm, matronly nature about her that makes her hard to dislike.

“Jessica Moore.” Jess says, extending her free hand. Ellen takes it and shakes it firmly, before turning to Tyson, who’s tired and barely staying on his feet.

“Tyson Brady.” He says wearily, offering his hand. Ellen gives a concerned look to him.

“Nice to meet you both. You look worn, why not take a seat?” She directs them to the nearest couch and helps them get settled. Jess wants to protest, but given how sharp a glare Ellen can shoot, she doesn’t particularly feel like challenging her.

Besides Ellen and the tall black man, the strangers include a priest, a middle-aged redheaded woman, a blond girl around Jess’ age, a sketchy looking man with a mullet, a black man and woman she assumes are a couple, and a woman in her thirties with curly black hair and quite a bit of skin revealed. Agent Henriksen, Jody Mills and the Warrens are not in site. Bobby walks back over to them, slapping a hand on Jess’ shoulders.

“Figured I should do away with introductions, so you don’t feel lost.” He says to Jess. “Ellen manages a Hunter’s bar with her daughter, Jo.” Ellen gives a smile, and the blond girl gives a nod. “Ash works with them, does hacking and whatnot for hunters. Graduated from MIT with a degree in computer science.” To her surprise, Ash turns out to be the mullet-haired guy she labeled a hick. “Rufus Turner taught me everything about hunting. He was my partner for a while, before we both retired.”

“More like, I decided I wanted to live a few more years.” The tall black man says, shaking his head. “Now you’re dragging me back in, I’m concerned that someone else thinks you’re qualified to teach them about hunting, Bobby.” Jess has to cover a snort, which earns her a glare and an accusation of treachery from Bobby.

“Pastor Jim, Annie, Isaac and Tamara are all hunters that are still active.” He gestures to the priest, the middle aged redhead and the young black couple. “And last of all is Pamela Barnes, best damn psychic in four states.” The brown-haired woman gives a laugh.

“Thanks for dragging me in here, Bobby.” She says. “Why not introduce the eye candy, and explain why you brought us here?” Bobby sighs, calling out for Zach and Becky. The Warren siblings come in from the kitchen, practically stumbling over each other when they see that Tyson’s awake and moving.

“Brady!” Becky splutters out, rushing towards her friend. Jess feels Tyson involuntarily wince at the use of his surname.

“Stick to Tyson, Beck.” Jess says gently. Becky looks confused, before remembering that she only had ever called the demon Brady. The Warrens sit down beside Jess, filling up the rest of the couch.

“Now, most of you know John Winchester.” Jess can’t help but feel a sense of satisfaction as those acquainted with John give groans of frustration. “But most of you, except Pastor Jim, don’t know his sons, Sam and Dean.” The redhead, Annie, gives a chuckle.

“I know Dean, definitely.” Bobby sputters.

“He’s just a boy, Annie. I practically _raised_ him.” Annie smirks, shrugging. “Anyways, the younger brother, Sam, was kicked out by John when he decided to go to Stanford.” Normally, the mention of Stanford earns nodding approval at the least. Not for hunters. “These four found out about hunting because of Sam. They went to school with him. These two are Zach and Becky Warren.” The Warrens wave slightly, seemingly unsure of what gesture to respond with. “They’re Sam’s friends. That’ s Jess, she’s Sam’s fiancée,” Jess feels many eyes on her, and gives a soft nod. “And on the end, is Tyson Brady, Sam’s last friend.” Ty gives a curt nod to no one in particular, and Jess feels him ease up at the fact that no one besides Jess knows the particulars of his relationship with Sam. “Ty was possessed by a demon up until two weeks ago.  Hasn’t been in control of his body since Thanksgiving two years ago.”

“How could a demon escape the attention of a hunter that long?” Ash asks, confused.

“Wasn’t causing chaos, wasn’t causing havoc. It was just watching, keeping an eye on Sam.” Tyson’s hand tightens on Jessica’s, and she sense him get ready to bolt. She wants to tell Bobby to stop, but instead she just pats Tyson on the back, trying to calm him down. “The demon that killed John’s wife, Azazel, was using the Winchesters in a game. They were pawns in a plan to cause Armageddon.”

“Wanna run that by me again, Bobby?” Rufus says. Bobby gives a sigh.

“Azazel and other major demons were going to cause the Apocalypse, using John’s kids. Part of the plan needed Sam back in the hunting life, so the demon using Tyson here came to kill Jess in front of Sam, except all the Winchesters are stubborn bastards, so Sam said no.

“Sam made a deal with the demon. If Jess and those around her were left alone, Sam would go into Hell that very instant. So, the deal was made, and Sam went into hell, and Jess here’s been leading the front to get him out.” The room is quiet, and most of those gathered look stricken. Hunters normally don’t look this nauseous. Then again, hunters normally don’t see people get dragged straight into Hell in exchange for keeping their loved ones safe.

“So, you need our help?” Isaac deduces. Bobby shrugs.

“I’ve got to train these four idjits, plus an FBI agent and sheriff who want to solve this case and start helping other people like we do. I need all the help I can get.” There’s a pause, before Bobby continues. “You can make the choice yourself. Just know by helping, you’re also getting to piss off John and every demon there ever was. But today, I just called you over to put something together for Jess.”

Jess’ head pops up in confusion, turning to Bobby.

“Huh?” The Hunter smirks, and disappears into the kitchen with Zach and Becky on his tail, before bringing in an enormous chocolate cake with the number 23 in green frosting. Jess’ face must still show confusion, because Zach leans forward.

“It’s May 2nd, Jess.”

She blinks. May 2nd.

Sam’s turning 23 today.

Beside her, Tyson buries his head in his hands, giving a sob. Jess feels her body tighten, and she fights to not cry like he’s doing in front of all these people. The room’s awkwardly quiet, as Jess tries to calm him down, while suppressing her own emotions. As much as she wants to, she will not cry in front of strangers. She knows full well the only reason Ty’s crying is because he’s far too exhausted to conceal his emotions, what with the guilt and the exhaustion from being possessed. The smiles on Bobby and the Warrens’ faces are quickly fading. Zach, surprisingly enough, is the one to act first, taking the cake from Bobby and putting it on the coffee table, telling everyone to help themselves, before taking Jess by one arm and Tyson by the other and dragging them into the study, closing the door over.

The minute the door closes, Jess slumps into one of the chairs, allowing the tears she’s been fighting to break free. God, she’s cried so much in the past few months she’s surprised the salinity hasn’t fucked with her eyesight.

Of course, her Stanford education in Biology should tell her that that isn’t probable, that it is barely possible. But with all she’s learned in the past 6 months about hunting, and Sam and his “destiny”, she isn’t really sure that impossible is a thing anymore. A hand is on her shoulder, and she looks up through her blurred vision to see that it’s Bobby.

“Y’okay, girl?” Jess gives a shake of her head, not really willing to so blatantly lie to him. After all, he isn’t prone to believe her, crying her eyes out _again_ for what might be the hundredth time in who knows how long, if she says that she’s fine.

“I’m sorry,” And she is, because she’s honestly been a whirlpool in the past few months, going from crying to fuming to bitchy and back to crying again. But Bobby just pats her head.

“I was the same the first year without Karen.” Karen. Bobby’s wife, the one he’s vaguely mentioned, the one who became possessed by a demon, the one he accidentally killed.

“I just – ” She clenches her fist, fingering the engagement ring, the last sign of love she has from Sam. “I wanted him back by now, Bobby. How’s he going to be when we get him back?” Bobby looks nauseous just thinking about it, but he gives a shrug.

“Hunters pop back from the worst situations, Jess. It’s what we do.” Jess snorts.

“How many pop back from hell, Bobby? You said it yourself, Sam’s been in there for so long who knows if he can recover?” Her mentor looks guilty, shifting on his feet.

“Jess, don’t be so down. He hasn’t even been in there a year.”

* * *

Sam has been in Hell for nearly 182 billion years. He definitely knows that none of the people he knew are still alive (except maybe Ty, assuming the demon that possessed him is still breathing.) He isn’t even sure if the Earth is in existence, or if humans are still a species. He knew the Apocalypse was supposed to be the end game, but since the plan with him and Dean failed, maybe there was a new plan. After all, Heaven and Hell had been planning the Apocalypse since humanity began and Lucifer fell, roughly 200,000 years before Sam entered Hell. They would have over 900 thousand times that amount to plan and engineer another apocalypse. Two brothers, both of the lines of Cain and Abel, the younger one among a group of abominations with demon blood.

Then again, Lilith was still kicking last time he’d heard from her, and the apocalypse would have most demons in high spirits.

So, either humanity and the earth have been eliminated by some other cause, or they had kept on going for roughly 182 billion years after their assigned expiration date.

Either way, anyone who’d try to get him out is dead, long dead, and probably in Heaven. Not like he interacted with the other souls of hell. For him, it was just demons, demons, demons.

“What’s the problem?” Na'amah asks, rolling next to him. Sam felt guilty, still does, every time he consents to this. Even though Jess and Tyson are long dead by now, it feels like a betrayal, and he can’t help but feel guilty. He shifts on the bed to look at her.

“They’re planning something.” He states. “They’ve pulled me off my torture for the past sixty years, they must be planning something.” The higher-ups of Hell, Azazel and Lilith and the whole motley crew of ancient demons – Astaroth, Alistair, Mammon, Belphegor and so on.

“I don’t know,” She says nonchalantly. “They might be. I’m high up, Baby, but I have nothing to do with that. I think you should just kill them all, become the king and have done with it.” He rolls his eyes. He loathes when she acts endearing. Like she cares. He’s a pawn to her, he’s a pawn to all of them, save his sisters.

And what nonsense, ‘I have nothing to do with that’. She’s easily one of the oldest demons in existence. According to The Archives, she was born a witch, the granddaughter of Cain, and decided to form a small cult that killed in God’s name and worshipped her as the high priestess of God’s word. Then came the inconvenient moment when she died, and was dragged to the deepest parts of hell.

“Come on, Prince.” She says, her eyes flashing purple. “Maybe another round will calm your mind.”

Thankfully, Meg bursts through the door at that exact moment, making the demoness jump away from Sam. She gives a roll of her eyes.

“Come on, Romeo, get your ass out of bed and put some clothes on.”

“Why, so they can tear through them when they’re torturing me again?” He asks, but still obeys, conjuring the garbs he was wearing earlier. He loves Meg, just as he loved Dean. He understands that she will never stop being Daddy’s Little Girl, the same way Dean was always Daddy’s Good Little Soldier. She would always obey, even if it means denying her own thoughts.

Meg appears as a young woman with dark skin and hair, in simple brown garbs. It’s an odd choice, even for Meg. After all, the way Hell was perceived allowed the demons in charge to create almost anything from their imagination. Of course, most things were the same. There was the dark skies and endless lakes of fire and clouds of smoke. In the distance, lightning struck, illuminating the racks where souls freshly condemned were broken. The air stank of sulfur, the palaces constructed of bone, the ambiance nothing but screams, boiling magma, and endless thunderstorms.

“Bit domestic, isn’t it?” He asks, giving his sister the once over. This earns him a kick in the shin. “OW!”

“This is how I looked, jackass.” Sam frowns.

“You were African?”

“Egyptian. Well, I was a slave of Egypt, so I guess that’s subjective. I had a Hebrew name – Maqqedah.” Sam paused.

“How’d you become a demon?” Meg shrugs.

“I made a deal – my family became free, and I was dragged into Hell ten years later.” There’s more to the story, but Meg isn’t prone to spill, so he shrugs it off.

“What’s Azazel want.” His sister shifts her gaze onto him.

“Just do  what he says, Sammy. Please. ”

* * *

Almost the entirety of the upper denizens of Hell are in the courtroom. Azazel and Lilith are occupying black thrones on either side of a much larger pale one, constructed with pillars of skulls and iron. Sam can’t help but smirk. No demon could ever sit on the throne. It was meant for the father of demons.

“Sammy , my boy,” Azazel says with a smile, eyes flickering yellow. “How are things going?”

“Just how you order them to go, Azazel.” Meg gives a groan beside him. Azazel just smirks again.

“Now, now, don’t be bitter, Samuel. You should be grateful you’ve had the reigns loosened a bit on the torture. That’s two opportunities we’ve given you.”

“What do you want, Azazel?” Sam asks, his voice devoid of humor.

“For you to pass a test.” Lilith answers, her form that of a small redhead little girl with pigtails. A snap of her fingers conjures up three people, bound in chains, between Sam and the platform where the thrones are situated.

“Brady?” Sam blinks in confusion, seeing the middle figure. The blond gives a sneer.

“You already know the middle one. The demon who possessed your friend.” Azazel explains. “He’s failed, recently. Been exorcised from his host, killed Tyson with him.” Brady’s eyes go wide, and he opens his mouth to protest, but it’s sealed with another snap from Lilith.

“The one on the left is Tom.” Tom’s as plain a man can be. Nothing that makes him stand out, with brown hair and roughly thirty years. “Also demon, also recently exorcised. Killed his vessel. But, before that, he was a neighbor of your grandparents. Spied for us, get the lookout when John and Mary were alone, if you get the drift.”

The last one is an honest-to-God clown. Paunchy, roughly fifty, in the red poofy hair and everything. He’s terrified, and even though Sam can’t understand why, he looks vaguely familiar. He’s clearly still human. He doesn’t have the same aura as the others.

“You remember Jack, Sammy?” Lilith giggles. “We’ve been saving him for you. You used to play games with each other, when Jack was at Plucky Pennywhistle’s.”

Sam freezes. Even after 182 billion years or so, he has horrifying memories of the place, specifically the Topeka branch. How for three months of waiting for Dad to come back from a hunt, Dean would drop him there so he could meet up with chicks and other kids his age nearly every day, how Sam would beg his brother not to. How he spent one day crying in the corner because he was scared and what if one of the kids was a monster and how was he supposed to know if he didn’t have Dean or his dad to protect him? How one particular clown tried to cheer him up, and Sam was starting to feel better. Until the clown pulled him into a room with no one else in it, and started touching him where he wasn’t comfortable, and taking off his–

And he begged Dean to not bring him back, to the point of tears, but Dean just told him to suck it up, told him it wasn’t that bad, and Sam had the same experience at least 5 more times.

So, a demon who helped Azazel force his mom into her deal, the demon who killed his friend, and the man who helped establish Sam’s permanent coulrophobia are all bound before Sam.

“What do you want me to do?” Sam asks, cocking an eyebrow.

“Break them.” This isn’t the first time he’s been asked to torture souls. Alistair in particular made the offer around every day for about 6,000 years, and was gifted with the same answer every time. Sam gives a weak chuckle.

“You don’t honestly think I can break the first seal, can you?” He asks, rolling his eyes. He’s read enough about the plans for the Apocalypse in Hell’s archives to know that the first seal requires a righteous man to shed blood in hell. Righteous being a title, for a Michael vessel. “It calls for a Righteous Man to shed blood in hell. I can’t be both the Abomination and a Righteous Man.” It’s common sense, honestly. The demons should know better.

“You have the genes to be a vessel for Michael.” Azazel points out. “You have the genetic capacity to be a Righteous Man. And you’ve lasted far longer than anyone else when it comes to torture.” He turns to Alistair. “Give him the knife, and start the pain. If he refuses, amp it up higher.”  The yellow eyes flicker, and he grins. “We’re going to wait until you break, Sammy. We can do this for all eternity.”

* * *

It goes on for forty thousand years, Alistair tearing Sam open, and offering him the knife to carve into Brady, or Tom, or Jack. Lilith and Azazel watch intently (evidently the rulers of Hell have nothing else to do).

It hurts beyond words. No matter how many years he’s been tortured, nothing could prepare him for what Alistair can do. Flay his skin, make his blood boil, rip out his eyes, pulverize his bones into dust, tear him down to a raw hunk of meat and them build him back up again.

Sam’s on currently his knees, the skin ripped from his back, blood so overfilled in his lungs that it’s actually pouring out in a steady stream. Thousands of miniature knives carve into his arms and the soles of his feet, and he screams as hard as he can with a clogged mouth. He collapses, and feels a familiar brush of magic as his wounds are healed. Panting, nude, and covered in sweat, he looks up to see Azazel and Alistair staring over him.

“Come on, Sam.” Azazel says, his voice amused. “Just one drop. That’s all we need, and we’ll leave you alone.” Sam wants to laugh, because are the demons _that_ blind, that they actually think _he_ could be a righteous man? He’s lower than any of them, sad as it is. He deserves this. He’s perhaps the only person who deserves Hell, because of how selfish and destructive he is. Ruining so many lives – Tyson’s, Jess’, Dean’s, his parents’ – he wish that he could just extinguish, like demons do when they’ve reached the end of their tether. But he can’t. He honestly doesn’t deserve to. He’s earned this eternity. On the off-chance that this causes the Apocalypse, Sam’s selfishness could ruin the world over, instead of just those around him.

Azazel extends the knife to Sam, dropping to his knees.

“You honestly are enduring torture, for these freaks? These monsters who ruined lives of those around you?” He asks Sam. “Don’t you think your family, your friends, deserve revenge?” Sam pauses, reaching up for the knife. Wrapping his hand around it, he gives a small nod.

Yes. Yes, his family and friends do deserve revenge.

It doesn’t ache as much as what Alistair was doing to Sam, but it still aches. Withdrawing the knife from his stomach, he holds his free hand up to the hole made by it, catching blood. Turning to a shocked Azazel, Sam extends his hand. And smears the king of Hell’s face with his blood.

“Blood spilled by a Righteous man in Hell.” Sam says with a sneer. “That do the trick?” There’s a pause, and Azazel’s face contorts in rage.

“I’ve tried to be nice, Sammy boy.” He says, gripping Sam by the throat. “But you’ve just tried my last nerve.”

“Dad!” Meg rushes forward, Ruby on her heels. “Dad, please, just let him prove himself – ”

“I’ve given him chances, Meggie dear,” Azazel cuts her off, a wave causing her to cough up blood. “But I think what will make him calm down best is a little buddy-buddy in the Cage.”

Sam’s heart stops when Azazel says Cage. He’s never met its resident, for obvious reasons, but he knows that if torture by corrupted human souls is hell, then torture by one of the oldest beings in existence doesn’t bear thinking about.

The looks on both Meg and Ruby’s faces portray terror. They shake their heads, begging, pleading. But Azazel disappears with Sam in tow.

They reappear on what appears to be a large plateau. Like all of hell, it stinks of sulfur, and has smoky black skies of thunder. However, there’s a freezing sub-zero that washes over Sam, the source of which is a large fissure in front of them.

It’s wide, running at least twenty yards across and who knows how far wide or deep it goes. But the strange thing about it is the iron bars running across it. Wide enough for a person to fall through, but obviously meant to contain an entity that’s very large. Azazel smirks, holding Sam over the fissure, as Sam still continues to fight.

“Give Padre my regards.”

Sam barely has a chance to fall through the chasm when he halts. Looking up, he can’t see the exit, or Azazel, nor can he hear the echoes of his screams. Which doesn’t make sense, as Sam had just slipped past the iron bars.

Suddenly, a brightness blinds him, and the chill he felt before intensifies, going down to his bones. A loud ringing fills his ears, and Sam practically feels his head split in two. Even with his eyes shut, he feels the splotches of light break through his vision, and in his mind, he hears a voice.

_Hello, Sam._

* * *

Thankfully, the party’s picked up, even without the actual Birthday boy. When Jess and Ty both feel well enough, they come back into the living room to talk amongst the guests Bobby invited. Everyone’s cleared out, the last few stragglers heading out the door. Currently, Jess is talking with the Priest, Pastor Jim.

“I looked after Sam a lot, you know.” He says. “He was a curious little thing. Always asking about God and Heaven. Even though I didn’t really speak to his family much later on, given how John was raising them, I still tried to keep in contact with him.” Jess gives a smile, nodding. She doesn’t have the heart to tell this Hunter what Heaven and Angels are really like, not when he’s trying to make her feel better about Sam. “So, when we get Sam back, I assume you’re going to have a wedding. Would you want me to lead the service?”

Jess’ smile is genuine this time, and she takes his hand in hers.

“Thank you.” The Pastor gives her a pat on the back, exiting through the door. Jess sees that at least half the cake is still left when she enters the living room, and she silently thanks Zach and Becky for ordering the cake. It’s the same she made for Sam his last birthday – chocolate, with slices of strawberry and banana. It’s rich, richer than what she’s had in a while, and her stomach is both grateful and in agony, she knows that it was too much for the long-term hunters to enjoy (I.E: More for her). Bobby, the Warrens and Brady are all sitting in various states of euphoria and drunkenness.

“How’d you like meeting everyone?” Bobby asked, nursing what’s probably his tenth glass of whiskey tonight, if speech patterns are anything to go by.

“That Pamela chick kept commenting on what a solid chest I have.” Zach says with a frown. “Making me feel really objectified.” Becky snorts, pushing him aside.

“Jo and Ellen seem nice enough. I thought that dude Ash was going to be a total hick, but he’s a genius.” She says, stretching out on the couch. Jess smiles, sitting down next to Bobby.

“Thanks, Bobby.” She whispers, squeezing his hand. “I know I’ve been difficult –”

“Trust me, you’re not difficult.” Bobby says with a snort. “Just wanted to make you feel more hopeful, remind you I still care about Sam.” Jess winces.

“I know you do.” She says, before turning to the silent occupant, whose flipping through what looks to be a cheap, dollar store-bought sketchpad. “What’d you think, Ty?” He’s silent for a moment, making eye contact with her before answering.

“It’s a lot to take in.” He admits. “I still don’t really understand the grasp of this hunting thing, really.” Seeing Jess’ eyes flickering to the sketchpad in his hands, he smiles softly. “Bobby said this was a sketchpad Sam drew in a lot when he was younger. He thought it would help calm me down, give an excuse so I wouldn’t have to make conversation.” He looks back to the book, nodding. “It’s pretty good, considering he was twelve.” He holds up a picture of a young girl, with blond hair in a ponytail and a peculiar pendant in the shape of a moon.

Jess smiles. She loved watching Sam draw. He often liked to pretend he was a terrible sketcher, but he just needs a few hours and he could produce a perfect scene. Tyson brings the book back down so only he can see, and keeps flicking through it.

All’s peaceful for a few minutes. They’re content to sit around in the silence, breathing softly. Then, Jess hears a sharp inhalation. Turning to the source, she sees that Ty is looking at the book, mute and pale.

“Mr. Singer?” Bobby gives a groan, sloshed out of his mind.

“Don’t call me Mr. Singer, boy. Only Mr. Singer there ever was was my daddy, and he was a selfish bastard.”

“How long has it been since someone drew in this?” Ty asks, his voice shaky. Bobby hears his tone, and snaps out of his haze immediately, looking sharply to the former possession victim.

“Why’re you asking?” The ex pre-med shrinks into the couch, looking guilty.

“Sam was the last one to use this? Like, when he was around sixteen?” The older hunter gives a nod, rising to his feet. Jess shifts nervously, eyeing her friend with concern.

“Ty.” She says softly. “What is it?” Her friend gives her a look of fear, before turning the sketchpad toward them with shaky hands. And Jess can’t help but lean in closer, to confirm she’s not hallucinating (not that she would know, honestly).

Because the picture is of her. The page is yellowed and rusty, the date marked May 2nd, 1999,  and signed S. Winchester, and yet it’s of her.

She’s in a white nightgown.

And she’s burning in a circle of fire.

**Notes for the Chapter:**

> Hope you liked it! Will try to update.
> 
> Just a few notes. Try to remember that in this AU, the demons have upped the time in Sam's specific portion of Hell to make 1 day equal to roughly 1 billion years. So, even though it's only been half a year on the surface......
> 
> Yeah. Sorry, Sammy.
> 
> My headcanon has Jess being a strange combination of Early seasons Sam and Dean when she's without the person she's close to. Sam in season 1 was angry and furious without Jess, prone to shouting and (coincidentally) crying. He also has his tendency to shut down and only see his objective, just like John (and Jess in this fic). Jess' Deanishness is her violence and her somewhat self-centered nature.
> 
> Ty's personality's going to be expressed more in the later parts of this particular fic.

**Author's Note:**

> Complain all you want about me making Jess every stereotype about Ivy-League level kids, but I don't care. Plus, I decided that Victor Henriksen is necessary to add to the hunting world, just because. And also, I feel that the Stanford hunters (Jess, Sam, Brady, Rebecca and Zach) will probably make all their aliases allusions to famous people in history and literature, as opposed to horror film directors or rock artists like Dean (guessing Sam doesn't care much either way).


End file.
